Moving away from Hawaii and trying to make renting my primary make sense. 

I have a STR which I renovated using a HELOC on my primary home.  

Know your comps, know your marketI bought the house for $500k knowing that I can put $50k of work into it and get an ARV (after repair value) of $600k based on comps that sold in the same neighborhood– I’m willing to put in the work to make this happen and can take my time since it’ll be my primary residence.As a house-hacker, you’re likely choosing a property based on one of your needs (close to work, near family, etc.).

As I hope to use the unit a bit myself, I also want to take into consideration the kind of community I'd like to use (which, conveniently, is also about to be primary parent demographic so I'm hopeful other millennials will be looking for similar things)FWIW, I'm happy to do reno on an individual unit, but was kinda underwhelmed by the community as a whole.I liked Champions Gate, but at my price point, I can't buy much that's appealing there.

Used a heloc on primary to buy first rental, i want to convert rental to a 30 year mortgage so I can use heloc again to buy 2nd rental.

Most require skin in the game on deals and work like this:Rates: 10% to 14% (Most Deals are 12%)Terms: 1 Day - 24 Months (Most Deals are 6 months)Fees: 2-5 points(%) of loan amount paid at closing (Most Deals are 3 points(%))Minimum Loan Amount: $50,000 Max Loan: 65-70% of After Repair Value(ARV) 100% Rehab Financing Available (Most Deals require 20% of purchase price down payment or cross-collateral)Closing Timeframe: 48 Hours - 3 Weeks (Most Deals are 10 business days)NO PRIMARY RESIDENCES, NON-OWNER OCCUPIED ONLY, BUSINESS AND COMMERCIAL USE ONLY.

I currently live in Valdosta and own my primary residence and 5 other rentals in the area.

My current primary was purchased in 2018 with a conventional loan.

We have also made countless memories at our primary cabin.

Contrary to your line of thinking here, instead of having the restaurant buy your steak for you or taking steak to the restaurant to have it cooked (for a markup), some might think its better if you bought and cooked your own steak.It does seem in some of the states, you can act as your contractor on a single build or your primary residence; so it would appear if someone can handle the travel between 50+ cities, may not necessarily need a markup GC.