It varies by situation, but a couple decent benchmarks are if it improves your rate by 1% or more, or you recover the refi costs in two years or less.

As for the HELOC, the more I research the more it matches your comment regarding using it for home improvements / flips so I may sit on that for a little bit until I educate myself further on those topics.As for raising capital, I have read the private lenders are a popular way and hard money loans which I do not fully understand yet.

Successfully turned 80% of rent roll from $650 rents to $1150 and drastically improved the NOI.

Among other things, these provisions prohibit the DST from doing things like making substantial capital improvements, refinancing, raising additional capital, and other things that are typical in real estate operations.This limits what DSTs can invest in and dictates how they must be structured. 

Even if you purchased the investment property first, at least you would have the cash flow & equity of your investment property (wouldn't recommend purchasing at market value in this market) to improve your financial profile and increase your chances of being qualified for a primary residence loan, instead of the other way around.

I should just give up on the pursuit of self-improvement and fall in line, so I don't hurt peoples' feelings and make their childhood trauma of feeling discredited and unheard flare up."

Additionally, strong credit, a solid track record in similar projects, and a well-detailed plan for the rehab can also improve your chances of securing favorable financing terms.

There are a few things that can improve, but overall the financial side seems fine.Buildium is okay, but they are limited to what banks you can sync with.I love Yardi Voyager 7s, but the down side of it is the lack of bank feed, it is nonexistent.

I've heard it recommended to tell tenants that you are the property manager rather than the owner because it can improve your relationship and they are less likely to come after you (Note: we currently don't have any issues and don't plan to, just being cautious). 

You have very little control over the use of the property, the HOA and costs, especially when it comes to capital expeditures and improvements.