Additionally, I do allocate a minor percentage of my net worth to investment with more growth potential, like land development deals.[...]Finally, what investment do you make to accomplish your financial goals?

VA loan, very close to no money down, but we did pay a little out of pocket to coverHow did you add value to the deal?

I understand that there won't be any cashflow but the loan paydown and appreciation over time hopefully offsets not having cashflow.Legal and Financial Advice:Do you have any recommendations for legal or financial considerations we should take into account when formalizing this co-ownership agreement?

The quiet title is normally necessary before any lender will make a loan against the property.  

And buying the other one with maximum leverage.This can be especially beneficial to you if the short-term rental you want to buy is positioned such that you could take advantage of a 2nd home loan. 

Are you approved for a loan?

Traditional Second Home Loan How did you add value to the deal?

Setting up something like this in a bridge loan to take on some of the rehab could be the best way to go, but most will want to see some 10+ experience to really get what you are hoping.Do you have someone with some "experience' in that space who might do a JV?

Contacted local DSCR loan officer and was told the best rates would be 7.325% with 30% down and that’s with two points.

If you close into a 30 year loan from the get go you will most likely pay a pre payment penalty of 3-5% so that strategy wouldn't make sense.