Yes, this is an unsexy option and it doesn't offer the same tax benefits, but you would benefit from reduced volatility (so long as you don't obsess over fluctuating stock prices), greater liquidity, stronger management teams and superior assets.

With a large portion of the incoming migration coming from international residents moving to the District, emphasizing improving and bringing back Washington D.C. sports teams to the city should create a strong desire for domestic residents to want to live near a fun, community engaging activity that is very relevant to those that live in and around the city.The District also has other programs it is running to make the District more attractive to live in outside of just working in the area, such as the Office to Anything program (Source) and the Housing in Downtown program (Source) which will incentivize developer through tax credits to convert office buildings into new construction housing and new construction retail properties, which should continue to attract more residents back to the area.D.C. also understands that with all of these big changes we have seen, the strategy and allocation of resources from the government moving forward should be reassessed to create a city that is adapting to the future trends to remain a safe and desirable place for residents to live.

I know how to use the basic features of QBO, as I do my own expense tracking, but my Bookkeeper is needed for the more complex entries (Loans, capital balances, reconciliation, data entry from PM monthly statements.)I spend almost 8k per year in QBO and Bookkeeping costs (Not including my accountant or tax prep.)

Who covers the tax bill when they don't pay the tax bill or the insurance? 

Honest... not great but we had other tax reasons to get into them.   

What are the tax ramifications of a sale, if any?

@Fulati PaerhatiA 1031 exchange is a powerful strategy to defer capital gains taxes and grow your rental portfolio.

Let's assume that the neighborhood is a C class and the median income of the city is greater than 3X of the market rent.Here are some of the considerations I've come up with so far:- Units are in need of renovation and capex is too high or not available- Unit quality is not the same as market - Seller is worried about losing tenants due to increase- Vacancy rates are high or filling units have been difficult- Rent increase would take multiple increases over multiple lease periods to get to market rate if seller is trying to retain the same tenant- Seller inherited property and just want to liquidate- Seller needs to liquidate quickly (financial burden, sickness, quick exit from land-lording)It seems like I might be missing a warning sign about a deal if they are selling with current rents that are under market; but again, this seems to be most of the properties I've underwritten.And in the same vein, what should I be worried about when purchasing a deal with under market rent with the intention of raising them after purchase. 

Since part of your property is a rental, I believe a portion of your mortgage interest should be a tax deduction unlike your other debt.

I recommend that you find a trusted or recommended Mortgage Loan Originator (MLO), who can give you options for property-based loans (mostly investment loans) and they don't use your taxes but the P&L of the property.