As far as having your mother as a paying tenant, i don't think anyone can answer that one for you, that is something you need to feel comfortable doing.

If you are comfortable with that real world risk and are poised with a valid exit strategy, go for it.

@Billy Gullett  go meet with your local HML create a relationship.. do not do phone or text do it in person.. show them what you have and where you want to go.the reason you want a local guy that knows the market is that after usually a few deals with them they may get comfortable to give you 100% financing..

I earn a comfortable six figure income.  

https://www.biggerpockets.com/renewsblog/2015/01/31/ultimate-beginners-guide-real-estate-wholesaling-2/ (Ultimate beginners guide to wholesaling)https://www.biggerpockets.com/renewsblog/2015/10/15/bp-podcast-144-getting-out-of-your-comfort-zone-and-kicking-butt-at-real-estate-with-danny-johnson/ (wholesaling tips)https://www.biggerpockets.com/renewsblog/2014/10/09/getting-started-real-estate-wholesaler/ (BP Podcast 091 Wholesaling)https://www.biggerpockets.com/renewsblog/2013/10/31/wholesaling-podcast-mike-nelson/ (BP Podcast 042 - wholesaling)https://www.biggerpockets.com/renewsblog/2013/08/29/flipping-wholesaling-plan-sam-craven/ (BP Podcast 033 - wholesaling)https://www.biggerpockets.com/renewsblog/2013/04/04/wholesaling-podcast/(Wholesaling & marketing)https://www.biggerpockets.com/renewsblog/2013/08/15/wholesaling-business-lamar-cannon/ (BP Podcast 031 - wholesaling)

I'm a beginner who is almost feeling comfortable enough (educated/prepared) to take my first shot at a rehab.

@Scott DillardI think you're really on to something here, my one suggestion is to come up with at least one more buying scenario ... you want them to take something, just design scenarios that work for you, and let it rip.

My strategy is wholesaling a few properties so that I can get more comfortable with the market and then Buy and Hold.

Has anyone out there worked with branding their properties (specifically with a certain aesthetic, design feature, or actual signage)?

This applies to Orlando as well as any other market you know well and are comfortable with the micro conditions.  1.