Most Ins Co's give discounts on the Premiums after a new roof is installed, even if just for a little while.BUT, if $ is an issue ... getting a "partial" roof shouldn't be a problem. 

Where you can SAVE money - is by teaming up with one broker or lender and establish a mutually beneficial partnership of return business and maybe earn your self a return client discount.

Accessibility features in the bathrooms?

Yes it means they won't repair anything, but that doesn't mean you can't ask for a price discount. 

This will definitely be my last...The hotel is currently getting rebranded and unit owners have the option to upgrade our rooms using the hotels "discounted and preferred" contractors for the "low price" of ~160k (again, the unit cost me 400k and is currently valued at ~340k).

If they are 3/1's I would 100% add another bathroom in each unit. 

There are several discount granite, cabinet and fixture places in NoVA and Baltimore but which one to use depends on your budget and timeline.

The check book control package look attractive, at $1095 after a July 4th $200 discount :-) https://www.broadfinancial.com/self-directed-ira-plans-custodian-checkbook-control/I will need to set up one with pretax 401K , then another with after tax Roth IRA, so, want to make sure to control the expenses/cash flow of start up costs. 

The rooms with private bathrooms get $1000-$1175/month.

I might came up with cash, but it has to be discounted.