Due to the passive nature DSTs are not meant for every investor and it is important to seek education to see if a DST is best suitable for you. 

I'm naturalized Toledoian now mate hehe

Labarr adds to the decades of high-level marketing and sales expertise a unique talent for helping others tap into their natural strengths.

I have all my systems and processes down to fix and flip a house tomorrow with the team I’ve built, i have private money lenders that want to invest but wanna see some skin in the game first.

Bottom line is I'm a bit wary of getting into this again and would really need to be sure that the first lien positions were solid, the borrower had enough skin in the game and the property was in an area where resale or rental would not be problematic in the event I had to foreclose. 

I think it's just the nature of this industry. 

It's a nice advantage that you have a background in property management but naturally the first step here is to keep saving, pay down some of your debts, and boost your credit score. 

Their expertise has value, they now have good skin in the game, and they will/should agree to share their thought process when they say "that's a good idea" or "that's a stupid idea." 

I think there might actually be a way to both grow your portfolio and respect his conservative nature using the 1031 exchange.You mentioned that your properties were held in cash. 

It only seemed natural to get into it as a full-time job.