I would like to attract high end clients or business that have regular people coming in.

Regular homeowners insurance will not cover the rental.  

The main issue is if you use a LLC to hold title, you won't be able to get a regular residential, conforming loan.

What’s people’s experience with regular vs section 8 tenants?

Analyze rental properties regularly, if a housing market is hot and the rent to value is no longer attractive, figure out how to move that money elsewhere to have better cash flow.4. 1031 exchange can be stressful, but 45 days is longer than I thought. i.e.

In fact, my company has been actively selling properties there since 2006 because of the regular flow of opportunities we find.So your choice of a market is good. 

If I wanted a full appraisal I could've got it, but paid the extra $400 or so.Helocs have more fine print than a regular mortgage. 

I do however manage 300+ rentals in the area and help our investors find new properties on a regular basis. 

Have a spreadsheet or accounting software and reconcile your bank, pm, and cc statements to the books regularly.

The return would be great for you. as for the other house, still chase it with just the down payment and regular conventional loan process.