I would invite you and your friend(s) to get educated together!

Any suggestions on how to get a loan(s) to buy and scale.

We set it up as an S-corp so we have to do payroll. 

One of the great things about them is they charge by the month and you can change your policy and terms on a monthly basis also.So, yes, you'll pay a higher premium for any month(s) the property is vacant. 

I tried to Airbnb a room in S.

A few tips I've heard repeatedly are:Have the students sign 1-year leases, no matter if they intend to be there over the Summer or not.Parents must co-sign on all leases.Learn the housing cycle for the school(s) you're targeting.

Fresh Shiny Paint.it was built in the 90's (no lead) but it seems to have a LOT of paint layers, much more than it should.How much paint is too much, and if it's too much what's the remedy for it?

If there was a TOD, then only the person(s) listed on the Transfer on death would own the property.

All of those sold comps that are showing properties with same size and age, are not updated (they still have the interior from the late 80's), which is why I am having a hard time to find comps that support my asking price.

Taking it a step further, I thought it would be a good idea to consider multifamily properties where I could rent out the other unit(s) to cover the mortgage (or even better produce positive cash flow) while reserving one unit for my vacation home.