Ugly ducklings can be the best investments if you're willing to put in the effort.

Are there specific considerations, tips, or challenges I should be aware of in these areas?

I am getting ready to close on a property in the couple weeks.

Please forward the contact information for any vendors with which you have experience or knowledge who can help exit a low-usage time share. 

See what the pool company has to say.

VA and FHA loans are basically the only assumable ones in the market place.

Hi Richard, welcome to the community!

Hello I'm looking for a good investor title company and/or real estate attorney in the Sarasota area if anyone can recommend someone they have used.

You may have to sell the whole property to access the funds in the IRA or 401k when you retire and for required minimum distributions. 

Go to Etsy and search for "rental property tracker," and you will find hundreds of nice spreadsheets to track 10-20 rentals, usually for under $10.Software has extremely helpful features like online payments, marketing syndication (click a button, and your property is advertised on multiple sites), electronic document review/signing, maintenance tracking, and owner reports.