The best thing you can do is to work with a realtor / property manager who's experienced doing Section 8 rentals and have good contacts over at CMHA to help you when issues inevitably come up.The process can sometimes take 2-3 months, but there are other programs like EDEN that can go a lot faster. 

Since your last residency was in 2020, you do not meet this requirement, so the exclusion likely won’t apply.You'll need to calculate the capital gains based on the difference between the sale price and your adjusted cost basis (original purchase price plus improvements and less depreciation taken).

I've been looking at single family home prices and rental prices in Austin TX and its suburban areas, and it feels like it's extremely unrealistic to find something that passes the 2% rule.

Many landlords, especially those participating in Section 8 programs like the Baltimore Regional Housing Partnership (BRHP), have noted a decline in tenant quality over the last few years, particularly since COVID-19.

Like I’ve mentioned countless times here on the BiggerPockets forums, wholesaling is all about sales and marketing.

I know they do not like to give HELOC on investment properties. 

A couple things you might look at is examine your local market and see what the other like kind properties in your area have that yours doesn't. 

I have searched the web to find some paid subscriptions like Monarch or YNAB or Empower.

Start with a tiny rental or a fixer-upper, use helpful tools and resources, and tap into loans like bank loans, quick cash loans, or loans from people you know.

So our hopes at reconsideration based on on the historical permit records are slim to none.So it looks like our only move here is to prove that the coach house has been existing as residential for at least 20 years and get an administrative adjustment.