I've been a renter all my adult life, but on moving back to the US this summer, I'll probably be buying a condo, so I'm getting an online education. Even if you don't need a mortgage, it might be worth talking to a few mortgage lenders who operate in the area that interests you. To write a conforming mortgage on a condo, the complex/HOA must pass the questionnaire provided by Fannie Mae/Freddie Mac, or the slightly different one provided by HUD/FHA. They have several concerns; you mentioned the biggest one, adequate repair reserves and no big pending special assessments. They also don't want to see too many rentals, or REOs and other properties that are vacant year round (25% of the units maximum.) A local loan officer might know offhand that this complex qualifies, or does not, or the manager of the HOA can tell you if they have prepared a recent questionnaire. Just as smaller local financial institutions are the ones most likely to write a baby mortgage of under $50,000, that's where you might find a lender willing to write a non-conforming mortgage on property they know, and keep it in their portfolio until you sell. I found one of those, a local credit union with an expanding deposit base, who will write an 80% LTV mortgage at 4% interest, of an amount as small as $25,000, but only for 15 years. I also found a small local bank which will do conforming mortgages, with a full 30-year term, as small as $35,000. It turns out different institutional buyers of conforming loans have different requirements. Some will take a small mortgage in a qualifying condo complex as long as they get to pad the interest rate ("high 4s," the loan officer said), and maybe charge an extra point or two, and maybe ask for 25% down. Others recoil from the type of place I will be buying like the Devil from holy water, saying, "A Florida condo? We've still got some from 2010!"
While looking over the candidate complex in person, it might also be wise to strike up a conversation with a gabby old long-term resident who knows everything that is wrong with the place. Just filter out the negativity and catch the issues for further inquiry.
(OT: I'm interested in baby mortgages because my Web browsing turned up spots in Florida where reasonably nice-looking older condos are cheaper than in the city in Ecuador where I now live ($30K to $60K.) I'm particularly intrigued by a small suburb northeast of Tampa, Zephyrhills, which has both cheap property and a below-average crime rate. There are even lower prices in more urban areas, but a few minutes of research usually found that the unit was an REO in need of rehab, and the area was a scary combat zone.)