We are currently dealing with a similar issue at a condo on Clearwater Beach, the HOA just told us that they are doing construction NEXT WEEK at the beginning of our peak season and the pool will be closed to boot for a month. 

As I've learned more about the markets I'm interested in, the first issue I found was that my ideal market (Charlotte) is super expensive, no multi family are available (apparently they weren't easy to build until recently bc of the city?) 

Local market volatility, neighborhood issues, local large employers and national economic changes can change your plans for you.

Only issue might be the budget.I think the two main questions I’m trying to answer for now are: 1) Do I want to do short term rentals to increase chase flows or long term so it’s a bit less day-to-day work?

Transferring the real estate to an irrevocable trust may help avoid Prop 19 issues and may also preserve your step-up basis for capital gains tax benefits.

Pretty simple to manage.You technically don't need a bookkeeping software for under 10 doors like a previous post mentioned.

C class B class  that has tenant issues that can never be solved? 

Law: Illinois has a law that requires (I believe) the insurance company to give a 'General and Special Taxes & Demolition Expenses' Form (Important info for this issue) to the city when claims/damages are over a certain dollar value.

I would also suggest talking to a couple of lenders now to find out if they see any issues as a result of the type of deed.

At this point they have no plans to resolve this issue other than increase taxes and replace wiring.