I moved from the Boston area to greater CLE in the summer...mostly to be closer to family. Renting a very nice house for the time being and dipping my toe into looking at houses. Need some advice on buying in a type of COL area I'm not used to.
Background: the CLE area market has historically been a declining RE market for the last 20 years. So much so that even the toniest of suburbs were forced to bulldoze some properties because they sat vacant. Between 2000 and 2015, housing prices fell 10%. (they fell 25% between 2000 and 2008). But up 25% since 2015. Over the last 5 years, commercial investment in the area is WAY up here and population flight is pretty much abated. And, RE prices have rebounded (finally) after TGR. However, CLE area still needs time to rightsize fundamentals: Greater job growth, less folks in poverty, fewer foreclosures, etc. I'd equate CLE to PIT 10 years ago.
Current: If I buy, it will be in of the 5 top inner ring suburbs for schools/stable home values. However, I have spent the last 25 years in Boston, where our RE market has become Seattle or Bay area insane. So this risk of losing money on a house is just not in my vocabulary.
Question: If we put COVID aside...are there specific analysis/buying strategies for buying houses in stable to slightly declining local RE markets? Of course, being a former financial analyst, I pull comps, factor in $$$ into key renovations into my offer prices, and so forth. And I'm not looking for a flip. But I want to do everything I can to guard against losing money if I buy now and decide to sell in 3/5/10 years time. I can pay cash or mortgage, either one, if that makes a difference.
Or, do I even buy? RE taxes are high here. My rent payment is EDIT: 12k per year more than RE taxes ALONE for a similar house. I think I would prefer to buy, but I don't know what strategies I should use TO buy in this type of local market

TIA