Since the previous owner is getting most of the proceeds does the closing attorney issue him a 1099S and then issue my company one for a much lower amount?

The reverse mortgage company wants buyout and I dont have over 200k to pay out.

Any PM software should be able to do everything you mentioned.I am not a PM but I am an Accountant/CFO for PM companies and real estate investors.

If you're going to run a successful business renovating houses, ultimately you being proficient at/and or managing said proficiency in estimating will be a crucial part of your underwriting.Google "how to estimate house remodeling" your hard work will be rewarded.

I’ve seen discouraging accounts about evicting S8 tenants and want to see if anyone has had success and how to go about it if she refuses to leave.

I feel confidant that your knowledge and expertise will bring you much success in your market.  

You can use the Bigger Pockets management finder tool to look up MTR management companies in the area and then I have a few recs I can provide if you are interested.Shoot me a message if you would like to discuss further and I can help you strategize to make sure you make the best decision possible!

The Costa del Sol is one of the world's most successful tourism success in the world ever.

That being said we as private investors can use this to our advantage and find some successes in POH parks or mixed POH/TOH parks. 

What I can say is that many physician + spouse combos have successfully done this and survived audits.