While this can maximize leverage and ROI, challenges include getting lender approval for seller financing, high carrying costs, and the pressure of short-term loans.

I am doing my best to accommodate and fix the insulation as well as see if there are programs in place to lower the cost. however i want to be firm with tenant as they are not compliant with paying rent because of the cost of the utilities.

This is my personal opinion, which probably won't be popular.If you are worried about the cost of hiring an attorney to create a proper operating agreement for your LLC, you probably don't need an LLC, and if you choose to use an online site to create an LLC, you probably get the protection you paid for.

Of course have your costs researched first bc the buyer will want to know how much it will cost them to buy.

The two deals with friends both ended poorly with friendships ruined and tens of thousands in legal fees and court costs.

While using financing does mean I don’t keep 100% of the profit due to borrowing costs, it allows me to take on multiple projects at once and operate in higher price ranges than if I were only using my own capital. 

Highly recommend self-managing so you can take advantage of a cost segregation and the short term rental loop hole!

I look at it through the lens of dollar cost averaging my real estate investments.

@Jay HinrichsI try to avoid historic districts at all costs.

Funny enough, I was going to suggest you move out of SF due to the high cost ;-) I'd suggest going down the SF condo route to start as financing for commercial units is a lot more difficult than residential properties.