Hahaha... love your writing style. 

I'm a software developer and very good with a spreadsheet and all, but I'm wondering if I could secure an experienced lender who not only can lend, but also provide advice on a deal like this from having financed similar situations before.Pointers to financial calculators for such an endevour and hotel/motel renovation-style lenders & contacts appreciated.Thanks,Matthew

I had heard as you described about if in same vicinity, if the homes were significantly different life styles that you could get 2nd home loan.I live in inland north county San Diego (Poway) and wanted a 2nd home loan for a San Diego beach property (mission Beach).

Be prepared for higher turnovers, dealing with parents and kids who have no idea how to live on their own (eg using dish soap in a dishwasher). 

Hi Ashton, I've been doing BRRRR style deals in the Midwest for the last few years (Memphis and Detroit).

Everyone has their own style of investing in RE as you see there are many different answers that were given.

Purchase price: $263,000 Cash invested: $10,000 3 Bedroom, 2.5 bath villa style home.

@Aaron Washington Most of the resort style communities in and around Disney/Davenport are going to have a spa, they are all built that way.

Not sufficient to build a dorm style house, but he had to add a very large ADU (the ADU looks much nicer than the primary dwelling). 

The bathrooms show better when the prospective tenants can see the full tile surround and they can get their own tension style curtain rod and curtain.