Paying for repairs

[NeonPegasus]

We have two duplexes caddy corner from each other. Both were built in the mid 80s. One of the duplexes has cedar siding that is rotten and needs replacing. The other duplex's siding has been replaced with hardiplank (we think) and needs to be painted. We're not sure if it ever was painted after it was installed. Both duplexes could use new windows. The windows in the unit with hardiplank siding have lost their seals and the trim around them was cedar and has lots of borer bee damage.

We do not rely on the income from these units and have been saving all of it.

I'm trying to figure out how to handle all of this maintenance.

It seems to make the most sense to replace the windows on the one with cedar siding at the same time as replacing the siding, especially since I'm almost certainly going to replace the cedar siding with vinyl and don't want to risk it getting torn up if I replace the windows at a later time.

The other needs to be painted and I guess I could put the windows off but there's no sense paying to paint or replace the trim when it'll be replaced when we get new windows.

I have enough money saved that I could probably do all of the maintenance above this year. It would be a stretch, though, and would deplete my savings in case other maintenance is needed.

Here are my options:

1. I could do the siding and windows on one house this year and the windows and painting on the other house next year, but I'm concerned about delaying the painting any further. Also, I would lose potential discounts for having a larger window job to offer contractors and/or having one contractor handle all the siding and window work together.

2. I could do all of the work at once and finance some of the cost with the contractors to ensure I keep a cushion in case smaller maintenance is needed that I can't finance at a favorable rate. I can also deduct the financing expense, I assume.

3. I could do all of the work and use personal savings to cover shortfall (our rental properties are not in a separate LLC).

4. I could replace the siding on one and paint the siding on the other this year and then replace all the windows next year so that the window job is bigger as a whole (but risking damaging new siding).

One other consideration is that I would like to use these expenses to offset income from the properties and keep our income under a certain threshold so we can continue to qualify for health insurance subsidies. Our MAGI without rental income would be around $110k so I think we'd be looking at a phaseout of the allowance for rental loss deduction. Maybe I could finance some of the work into 2018 and pay it all of at the beginning of that year so I could offset income from that year?

Your thoughts and advice are welcomed.

[iowagirl]

I would replace the windows before the siding is replaced. If you are able, installing vinyl siding is not that hard. I did my last house mostly by myself. You can probably find good instructions online now but back then I bought a book because the internet wasn't what it is today.

You can still paint the other house and do the windows later if you need too. Would caulking then get you by for a year or 2? You would have to repaint around the windows but would that be a big deal? The contractor will probably do that for you when he puts in the windows.

I probably wouldn't try to do it all at once. I would hire the neighbor kid and his friends (assuming you have one that will do that) to paint the house to save some money. That being said I borrowed a paint sprayer and painted my chicken house and shed myself because hate paying someone to do things I can do. I bought 5 gallon buckets of paint on sale, cranked up some music and had a good ole time.

You have to determine how bad you need windows and siding. Keeping the other one from rotting would be first priority but look it over really good to be sure that will take care of it. Will the rotting siding be ok another year, is it that bad or could you replace the piece that is rotting until you are ready to spend that much money?

IMO I wouldn't deplete my savings all at once if it isn't necessary.