The mortgage on this property is way above what I can rent to a family.

For STRs, material participation rules apply, and STR income is treated as non-passive, allowing losses to offset active income.This post does not create a CPA-Client relationship.

I don't have enough investor buddies around and my family would have zero interest. 

My family consists of my wife and three kids, and I’m currently the sole earner.

DSCR or Fannie/Freddie loans can go up to 75% on single family homes, multi family homes (2-4 unit) max at 70% if you stick with Fannie/Freddie.Other things to consider would be:Paying points for a lower rate vs higher rate with no pointsIf going DSCR - Prepayment penalty term (0-5 years)The lower the loan size ($200-250k and lower), you should consider paying up to 2 points and doing a 5 year prepayment penalty if going DSCR.

S8 tenants often have less of a support system as family members might be in the same situation.

Is multi family a better place to go than land? 

I grew up in North Florida so I have a lot of family, friends and business contacts in that area.  

If you're talking about single family homes/ duplexes etc. the neighborhood it's in will generally give you the risk profile.Hope this helps.

Investment Info:Large multi-family (5+ units) commercial investment investment.