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

Congratulations on achieving your goals on this piece of property. 

A well-thought-out property management plan, ongoing learning, and optimization are all necessary for building a successful real estate portfolio and achieving financial independence.Good luck!

Your Core 4 Real Estate team will play a very important role in achieving your goals.

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).

Ultimately, the decision should mirror your financial ambitions, how actively you're looking to manage your portfolio, and your risk tolerance level.Take some time to reflect on what you hope to achieve with this investment.

I've found that it's nearly impossible to achieve without one in place.

With the right lender, your 300K can achieve much more than merely purchasing single-family residences with cash.

Thank you,Steve          Hey Steve, that is an awesome goal and can be achieved over here in Rochester.