I've talked with some at length about my real estate goals and get positive feedback, but I get the feeling that I'm on my own financially at least until I've got a profitable deal or two under my belt.

What it said in that book really made sense to me but at the time I thought there was no way I could do anything about it to start changing my financial life while I was in college so I put it aside amid 22+ credit semesters of college and working part-time jobs, while also always being rehearsal for a play or musical as a theater major.

An LLC may be the perfect route for one person while an S-Corp may be perfect for another.While on the surface, both are doing the same type of business, the facts and circumstances regarding their financial and tax goals, their other sources of income, their tolerance for regulation, their family status and their retirement goals may be vastly different, which would affect the type of entity that works best for them.Taxes are not a cookie cutter, one-size-fits-all topic.

Are you financially strong enough to carry both mortgages in the event that you need to let your current SFR season as a rental? 

And if the builder is seasoned and/or has good financial resources in place then you should be fine. 

Continue to learn, network, & most importantly work on your personal financial situation.

In my quest to reach financial freedom, I have started many businesses in the past and failed at every single one of them. 

I know he is in a financial situation where the expense is not an issue, but morally I feel a sense of responsibility to cover some of the costs out of respect. 

It would not be difficult to obtain a property with my financial situation.

If I had a excellent tenant that I had for a year or more I would, under certain circumstance, allow them to do short term rentals.