Unfortunately, with the growth in our area over the last several years, they are completely booked. 

We have had several clients buy new STR properties in the last six months.

I'm looking for any tips or advice from anyone who's started in the last few years on what has worked well for them.Are there any marketing avenues that work best?

We have been able to find a few in the last year and many others are too. 

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.

.* I did this entire process in the last 4 months and take on individual opportunities.

But say a $10k heating system that should last 25 years (300 months), that alone is $33.33 per month ($10,000/300), even if it was just replaced yesterday since it will need to be replaced again in 300 months.

I been looking into either property abroad, homesteading/self sustainable home for myself, building a community living with a self sustainability situation with others, buying property abroad with a group of people I decide I trust enough to do so with (my inspiration for this last one: https://tynan.com/empire/), just go back to my original idea to house hack first, or a combination of the above.

Assuming he does not do anything like a 1031, he will be taxed on gains (assuming he has not lived there 2 of the last 5 years). 

Last Autumn I had the pleasure of finishing up the self designed and custom built-third unit in my 4 plex to rent out as a midterm rental.