Use the advanced function when you get to rental income and input each individual rent.

If fix the pool, I cannot charge additional rent as I am already capped and I will be stuck with maintenance costs and I can't help but think that if someone drowns in a functioning pool and if it turns out that the landlord could have done "something" whatever that "something" is, he may be on the hook for a major lawsuit.

There is always a buyer out there and it just is usually a function of price.

There are a number of programs offered by lenders which may be able to help with part or all of your ask.

Some of them have some great HELOC programs. 

The parameters of the loan program you use to refi will dictate how much cash you will be able to pull out. 

humidity is also a thing, it's common to see dehumidifiers in a lot of these older basements to keep the crumbling and dampness to a minimum.2.) read up on 4D and Section 8, so you're aware of what's involved when properties are participating in those programs.3.) st. paul calls their rental license a COO - certificate of occupancy; maintained by the fire dept. 

The Section 8 voucher program is money for the tenant to help with making their rent payments.

Is there a training program that is better for someone who wants to invest in multiple states or does that really matter if my goal isn’t to agent for others right now?

Got licensed so I could talk rate, loan program, etc.