I self-manage and produce $700 in pure cash flow each month.Lessons learned?

Typically what I advise clients is to self manage your first 2-10 units hire your management for 10-100 units and then have the management company scale with you when you get to 100-200 units.

With regard to your "DST" and as with many highly structured tax vehicles that have a potential "self dealing" quality to them, there are a number of potential potholes you can easily step in along the way (e.g., constructive receipt doctrine, effective control over nominal 3rd party relationships, lack of genuine risk bearing and compliance with transactional terms, etc.).

Same owners, same management (self managed), both STRs.

ROE (rather than ROI) tells you the rate at which your current net worth is self-perpetuating.

@Brandon MorganI self manage my 29 SFR and run into this all the time.

Perhaps I make 5-10% if forced to sell if I’m lucky, break even at worst.2) I’m VERY glad I chose to invest in my local market (and not OOS), because I know which neighborhoods to buy in, and I also can self manage, which saves a ton of money and I am able to develop local connections, which helps me buy at a discount.

I prefer to self manage because its insanely cheaper and honestly not a huge time commitment.

"Wholesaling", where you only find the deal for someone else and don't close on it first *your own self* is selling real estate and requires a real estate license here, and in many other states.

If you only look for the input you want, you won't get the feedback you need.Self-awareness and self-analysis is a crucial part of investing.