You'll be asking yourself what these extra are worth now, each year when you contemplate rent increases, and each turnover, so it is good to have facts and data to support your gut feel.Keep in mind that if you stay lower rather than pushing the price, you'll get a better applicant pool to be able to choose from.

He's willing to let it go to me well under market value ($150k, comps support $300k) and he offered to carry financing (seller financing).

Have you considered going that route and run the numbers to see if it supports the interest payments?

I have a little experience with the utilities and it took an act of God to get a support wire moved so what you are looking for is the definition of a long shot.

If the bank is requiring this kind of outside cash flow support, I suggest you find another lender.Your forecast of a 1.5X at only 25% occupancy on student housing does sound a bit optimistic.

What is really holding me back is the lack of support from any mentor or experience person.

Lionsgate real estate group, It really supports its agents, there are no monthly fees, they have a dedicated marketing team and all of your marketing is done for free.  

At the moment, I don't think it will pass VA inspection standards, the porch stairs is rotten and support is broken. 

I thought the automation offered by VRBO and Airbnb (SEO, Listing and photos management, price management, calendar management, inquiries and in case of dispute, some support) was exactly why we were paying them, but you are right if it brings you additional revenue, then it makes sense.And yes on top of what we said above about the vrbo vs airbnb sweet spots I do see the same thing as you when you say: " My perception is that people using VRBO are middle aged people that don't mind spending money on a nice place. 

I am a strong supporter of cash flow style investing over the appreciation style models.