Seems like you can get there quicker by focusing on setting up short-term rentals, and perhaps ones that don't need extensive initial rehab.

It also allows us to gain experience with managing rentals as it's built out and we don't have to go looking for deals to scale the initial portfolio. 

My strategy is BRRRR with the initial purchase and rehab using private money, then pay then back with a cashout refi after 6 months, so maybe that is something you could look into.

Tenants staying put for 16 years typically falls on the side of charity. 

Initially, I was hesitant to accept due to the cash flow that this property provided; however, a very tempting value-add RV park also popped up simultaneously with this off-market offer on the house.

Just a couple of initial thoughts I've been considering, but I was curious what others might be doing to further maximize their vacation rental in different, creative ways?

I guess I just wanted to feel philanthropic I suppose - but perhaps a waste of time… Nice of you I guess, but it's not wise to mix business and charity.

Initially our offer was lower than some of our competitors.

I did use the same lender which hired the same appraiser for my initial purchase so that could have been the issue. 

My role would be anything behind the scenes dealing with LLC paperwork, accounting, initial funding, etc (will not be involved with showings, or anything dealing with a listing or sellers or buyers)The friend with the license and owner will deal with all real estate requirements of the business.