Trying to narrow down which strategy will best suit our goals and lifestyle is my current focus, and I am looking forward to having meaningful conversations here on these forums.

I'd encourage you to weigh all of your options before making final decisions.

It may be required on a Commercial, DSCR, or Hard Money loan but I would encourage you to speak to multiple lenders to find out which specific loan program you need for your goals and qualifications. 

@Julia Lyrberg Thank you for the encouragement, I know it’s not the greatest score but I currently have around a 740 so I don’t think I need to be super concerned on that end but yes I’ll definitely be trying to tidy up my finances better.

In fact if you disagree with some of these comments, I would highly encourage you to reply to them with your own experiences and opinions as well. 

On the tax side, I would encourage you to partner with a knowledgeable real estate CPA who can guide you through the transaction to ensure you can meet the qualifications of the STR loophole.

I'm not currently encouraging investors to do unincorporated JeffCo for that reason - they've become more strict/unfriendly over time.

Two things I would encourage you to ask yourself & ponder (essentially count the cost): 1.

By the time you have 4, 5 ... 10 properties, it makes it worth the time to systematize and gets some meaningful current income.In short, if I just wanted to invest the money, I'd look into a syndication. 

I'd encourage you to evaluate the REIT first, then the DST second.