This would obviously reduce my cash flow on both properties, as I would be paying the minimum HELOC payment plus extra towards the principal to pay it off quickly.

First, estimate what the renovation would cost, how long it would take, and how much extra you could potentially sell the property for once it’s fixed up.

If you plan to live there in the winters, you might have a hard time doing long term rental outside of that and finding a new tenant every summer.

Is that available to scale up and if there are investors,  resources to manage that side if the business.I imagine a $60M/year Lending business will need systems in place and more than 1 extra person.

Quote from @Kristi Kandel: Helping LA Communities Rebuild After WildfiresWhen Hurricane Ian hit Fort Myers Beach in 2022, it changed our lives forever.

@CraigIf you have two offers with that high of down payment already you must be living right!

Quote from @Brendan Doherty': I’ve read in books of people getting past having to live in the property they own so they can rent all units year one of ownership(living on the property with an rv).

The reality is the opposite - if it's not in writing then the PMC doesn't have to provide the service or can charge extra for it!

As I grow I will hire a virtual assistant to take a few more tasks off my plate to allow me to live the same lifestyle. 

The least states:"Tenant shall pay a "late charge" not in excess of five (5%) percent of the amount in arrears for each month the arrears remain unpaid if any Rent is paid more than ten (10) days after the due date thereof, to cover the extra expense involved in handling delinquent payments.