Would only do if double your $21/1,300 sqft annual revenue after costs.

In DC and Boston both, my properties values and my rents double on average every 10 years.

The AIO and 1st lien or HELOC strategy is not meant for financial undisciplined people but you're right if you're undisciplined a fixed loan may often be better because typically that person cannot put extra principle in their loan anyway but they might frivolously spend all their available line credit anyway.Where I'm from, once upon a time (not so long ago), home loan interest rates were well into double digit interest rates.

My Class A Indy suburban home (Hamilton County, which has the highest median income in Indy) has doubled in value from 2013 to 2021, great tenants, excellent schools, very few problems.

I feel like it's double what it should be, but feel that I should just find someone new rather than have someone justify their pricing to me.

But if there is ample room in the bedroom and you can take a single sink to double vanity, or add a dedicated water closet, or take a 3x3 shower into a 3x5 or larger, making the bathroom more luxurious, than I could see a good ROI on that.While the area may be very nice, the price point you are talking (and I don't know the specific market) is borderline starter home prices.  

(New roof, paint, etc) and proceeds even if we paid capital gains taxes could pay down other properties debt including adjustable HELOCS which would double our annual income but of course we would lose a door. 1 property is currently vacant and I anticipate at least $10k to refresh including new gutters.

Wholesaling is when you assign a contract and never take ownership, or if you double close the end buyers funds are still what purchase the property for that brief moment when you close on it and then they close on it. 

Contribute to your HSAIf you are married, you can do 2 & 3 double. 

Investors like to double their money and recycle it again to the next.