@Tom Rairdon If you’ve owned your short-term rental (STR) for over a year, it likely qualifies for long-term capital gains (LTCG) treatment, taxed at lower rates (0%-20%) compared to your 33% ordinary income bracket.

Experience Purchasing from Non-ProfitsPurchasing property from non-profit organizations often involves additional considerations compared to typical transactions:Decision-making process: Non-profits often have a board or committee that must approve property sales.

The rent-to-price ratios in many neighborhoods are strong, and the city’s population is finally growing again after decades of decline.One thing that stands out to me is Detroit’s median home price—around $95k—which is far below comparable cities of its size in terms of population.

I looked at the comparable home sales and felt like the prices he wanted left me with enough room to make some money.

What happens to the 'comparable value' if the area is uninhabitable or a community that won't return for years? 

Multifamily properties do require more management overall and typically appeal to a smaller, investor-focused buyer pool.At my stage, I prefer small MFH over anything else because of the stronger cash flow, scalability, and the more forgiving capex compared to larger MFH, but the best option depends on your goals and strategy. 

You look for comparable sales for other distressed properties that are similar and nearby and also counter that with finished version comps so you can see what your perceived spread could be.

There are plenty of deals in Philly on and off-market from wholesalers, who are pretty decent in Philly compared to other places.You will need to get your GC license here and learn the permitting process and necessity here as well.

Properties are sitting on market for a bit longer now that supply is slowly creeping back up. 50 days isn't too terrible compared to the greater PHX area. 

there are ways to get around the highest and you also need to take into account the savings you will generally have on the purchase side when compared to other regions.