Hard to advise without actual numbers. If you bought the homestead, could you cover the costs of the remodel and upkeep, along with all of your other living expenses, out of your wife's salary? If not, how much would you need to bring in as a handyman to make ends meet -- and how much would that cut into your time to do all of those other homesteading things you're planning on? Would you have other job options if it turned out that people weren't as willing to pay for handyman services as you hope (after all, the folks who are advising you on that have their own vested interest in getting you to move and buy the property -- are they really going to tell you that, no, no one actually wants/needs handyman services?)? Do you know what the ongoing costs would be to support a productive homestead, including things like equipment, repairs, maintenance, additional workers to help with planting/harvesting/etc., even down to things like cleaning the B&B between guests? What about any licensing or regulations -- do you know/can you find a local lawyer to advise you on that?
If you want to turn the homestead into your primary business, then you need to go into it treating it as a business, rather than simply as an opportunity to move closer to home. It is a huge lifestyle change that will require a lot of effort and money on your part to succeed, so you should be realistic about the likely costs and potential profits from that business. Put some time into doing research and getting as detailed with your projections as possible.
My biggest question is really whether you've always wanted to homestead and this is your opportunity to do so, or you really want to move closer to the family and this opportunity has come up. If you really want to homestead and this is your chance, then do your research and go for it. But if the driver is to be closer to family, and homesteading kinda sounds interesting, think very very hard, and don't be afraid to keep looking. It's easy to rationalize choices that get us what we think we want, but when your goals are clouded that way, those choices can be fairly off-track. And if you need to give up a life that you're currently very happy living to do that, there are some big potential downsides if that choice doesn't make you as happy as you hope it will. So do the best you can to be objective and challenge your own thinking.
Also, 4 hrs isn't actually that close -- sure, it's closer than you are now, but it's not like you can pop over to watch a kid's baseball game, you know? It's still a big production, and as busy as you will be developing and managing the homestead, you're not going to have nearly as much time as you'd like to do those kinds of trips. So if the driving goal here is to spend more time with family, look for other options that are a lot closer and will actually enable you to achieve that.
