Giving my tax guy a benefit of doubt, he has known me for 12 years to be a "stable saver" and i think the idea of draining my savings into a new venture that excites me and changing career directions was alarming for him.

Happy to point you in the right direction / share some info that might be helpful as you start expanding into your own projects 

That cash flows well above the PITI payment including management fee's and other factors.If you really want to spend more money $850K to $1.25M you can get a 2-4 unit directly on the beach which are booked 6-8 months in advance.

Have you thought about hiring a handyman on an as needed basis and simply have the tenants call the handyman directly if there is a problem?

Just looking for advice or a direction.  

Direct lake front properties about that size are around $200-250 a night.

If any local Houston investors or realtors could point me in the right direction that’d be appreciated. 

Real estate is a vast industry and requires a clear sense of direction to succeed. 

Anything 5+ units is valued on the NOI and cap rate (typically), so it would apply if you turned the property into five units with two beds each.

Here is the situationCottage - seller asking $300KSold in 2021 for $225K, seller put about $15K into itBuilt in 1940s, very few updatesNeeds new roof, old 2-wire electrical, original walls, and has an $8K assessment by the association about to come due.700 Sq FtPart of an association owning shared private beach access@ $300K it is $426/sq ftComps (all sold in last 6 months)Cottage sold (to this seller) 5 months ago for $425K @ 872 sq ft = $487/sq ft"Direct" lakefront property part of same associationBuilt in 1940s, some updates3 other comps I've seen that are larger that have similar associations w/ shared private beaches that are "near" lakefront on the same lake.1.