Planning ahead.

It will eventually need painting and we have set aside money for something like this for that property, however, can't decide if I should wait another 5 years or go ahead and do it now.

I understand the subordination now (thanks for the explanation), but if something crazy would happen in the next 2 months where the IRS wants to lien the property, that would still go ahead of the lender in lien priority, correct?

I have already green lit the homeowners to go ahead and get ready for the move so the house can be vacant the day of closing.

Doing your research ahead of time to make sure you are getting a fair deal will help ensure your success as a landlord.

I did get a warehouse for the separate business and shooting for the 200-250K so ahead of the goal.

The first thing you need to do is start learning the business, and how it works, not getting ahead of yourself.

Ahead of a lot of us already. 

After you purchase the house, I do not believe the FHA has any prohibitions on you having "roommates" (as long as you occupy the home as your primary residence).But you won't be able to count that income ahead of time to qualify for the loan in the first place. 

Some people including myself like to plan ahead and usually those tenants that do are the best ones to have.