If getting another $100k in cash unlocks a large flip profit to keep scaling/injecting capital into your business or a great cash-flowing property that outweighs the increased capital cost on the triplex, then go for it.  

What I can tell you is that if you get caught renting out a unit like that my guess is fines will out weigh the benefit.

The financing obstacles have to be priced into the pro-forma   but I generally find the pricing concessions I can achieve on these acquisitions due to lack of market interest far outweighs the financing obstacles. 

Just getting to the point where my RE investments outweigh my expenses.It's awesome that you are killing it.

You should consider whether the potential property value increase or other benefits outweigh this loss.Here's some generic beginner advice to help you get started.1.

If I were you, I'd focus on commecial assets (5+ unit multifamily) and possibly partner or JV with someone who is stronger on paper to outweigh some of your weaknesses.If you were targeting residential properties, you can also get a co-signer who can help get you over some of the barriers you face.

"Off market" can be good if it fits into your strategy of the time and effort outweighs the actual cost savings.

We got dinged with one that was our fault, but felt the punishment way out-weighed the crime.We took on a handful of properties from a new client. 

Yes, but the positives usually out weigh the drawback. 

There is always a cost to invest whether that is buying a new property or investing passively, however if the DST performs like projected the appreciation upon sale could out weigh those costs.