We want To owner occupy a multi family property so having her income too will really help to qualify. 

I have a multi family property connected to septics. 

The issue imo with DSTs is that you’re buying into a market where a lot of commercial RE is presently priced high, and some is going down in value too.You should do a thorough analysis of the tax impact. 1- definitely try to time sales into two separate tax years2- I’m unclear why you expect 30% cap gain hit.

Investment Info:Large multi-family (5+ units) commercial investment investment.

(I'd like to be close enough to the property should any issues arise but will have a property manager)Thank you and apologize for all the questions but it's been discouraging to say the least so far.

The issues I am seeing, especially with newer HOAs make me think that you should almost never buy a rental in an HOA.One HOA in north Texas tried a few years ago to prohibit Section 8 rentals. 

Your only issue is that STR management is costly in Austin, up to 25 percent.

There's specificities for SFH, multi res, industrial, commercial, self-storage, hotels, etc.

For your biggest concerns, #2 is really an issue for a contractor to discuss with you.

Make a list of your current frustrations and see if the new software addresses those issues specifically.