They also offer very little in expected appreciation, renter demographic is not ideal, and don't offer as much tax benefits as RE.

This would make an ideal rental - hopefully you have somewhere else you can go without increasing your cost of living too drastically.

Speaking in broad strokes (I'm not a lender), a portfolio lender will have their own guidelines and not be glued to the freddie/fannie guidelines for DTI.

Ideally same title company.Best of luck! 

Ideally, you would want a land specialist, but they may not accept a low commission.

Ideally, someone with knowledge of self-directed IRAs, Solo 401Ks, and the various tax implications.

Ideally there about 5-6 markets I'd like to be in but right now since my team is thriving I'd like to give them more doors so that they prioritize me more and so that they make good money at the same time.

Ideally I want to make it so he does not have to pay anything back to me.I like the Joint Tenancy with Right of Survivorship idea!  

The VT property is actually an ideal property to rent due to the lack of rental housing in the area, and it's close to two universities. 

@Rob Randle, I believe an ideal loan option (that for some reason doesn't seem to be very well known) is the Fannie Mae Homestyle loan.