That need could outweigh their desire to protect your best interests.Not saying there investment here is a bad thing, per se, just raising this point so that this one element of the deal doesn’t tip the scale to you investing if you otherwise might not.

I am potentially interested and from the initial conversation looks like something I'd like to move forward with. 

She moved to France and became a Citizen and never came back.

Generally, title will take longer than that to approve but, you can amend the contract with the seller to move it up.

After the tenant’s year lease is up, I plan to move out and rent the entire building.

He has agreed to pay off the taxes owed.I'm not what steps are required for us to move forward. 

Run through some of the features you will need like setting up a property, moving in a tenant, receiving rent payments, and publishing online applications and see which one works the best for you. 

I have the opportunity to turn my first home into a STR once moving into a new home.

We also had an extra umbrella policy.Now that a few years have gone by and we've obtained more assets, meaning we have more to loose, it's made since to start an LLC and start to move things under its protection.Even if you get a good management company, which sounds hard to do, you'll still have to manage them and make sure they're staying on top of things.

Can anyone give me any tips with regards to dealing with owners who are going to finance a deal?