Not looking to move out of current home as it fits us perfectly in our current season of life (with a 3.375% interest rate).

You need a DSCR lender with a lower seasoning period.

A seasoned builder could obviously do it for less at scale, but you'll pay a nice overhead to bring in a builder and you won't get builder prices.

I clean our grill a couple of times a season when I head over.

I’m a seasoned wholesaler and a GC by trade.

Just keep in mind that if it is an older house with cast iron pipes and you lift the foundation, those pipes are likely to break and need replacing - partial or a complete repipe. 

The  unit is rented consistently and is functional but also needs upgrades, new siding (has 2 layers), Some rooms could benefit from re-wiring and more insulation,   Painting is always an issue as it is not plaster but older thin wallboard. kitchen is fairly new, bathroom could use upgrade, upstairs bedrooms have some pitched ceilings but I don't think based on the foundation/construction it is a candidate for a full second story and it had a new roof a few years ago.

There are still plenty of older, small multifamily properties with lots of value-add opportunity there.

All the things you can't see will come back to kill you in a 1912 12-plex if you aren't a seasoned apartment investor.

Unless you stay often during peak season, then you might not make as much revenue on the STR.