Ideally, I would like to buy in the Catskills since it’s close by, a popular year round destination from the city and has a history of vacation rentals but I know there’s more and more talks of regulations so I am open to other areas and would love to hear your thoughts/experience on the area.Would love to connect with anyone who has interest in the area and the short term world as well as agents familiar with STR who could help us in our search.

***Self directed IRAs have become very hot among investors with the rise in popularity in alternative investments such as real estate, gold, and cryptocurrency.

It's in a popular year-round tourist destination with a shortage of hotels and heavy restrictions on STRs. 

https://www.biggerpockets.com/blog/short-term-rental-loans-a...DSCR Loans: Terms to Know When Working With These Popular Rental Loanhttps://www.biggerpockets.com/blog/dscr-loans-terms-to-knowWhat’s Next For DSCR Loans?

She thinks that open houses which have always been the bane of listing agents ( NO one likes to do them and you usually pon them off to starter agents.. ) Will now become very popular as buyers will have to go to these for not just kicking tires but to actually get to see a house they want to buy..

Sorry to hear this.I would always say that "There is nothing wrong with any property as long as the price is right".Granted, some are not salvageable and the deal doesn't make sense even if the seller paid to me to take it lolOver the past 10 years I have witnessed many investors trying to do the same thing as you.Purchase from afar without buying turnkey and trying to do it themselves.This has been popular especially the last few years.Not many succeed unfortunately or they don't succeed in my eyes as they are into deals for much more than what they should be.There is a big trend going on where folks are made to "feel involved" with the purchase, rehab and property management process.The properties look great and off-course they do as rehabs cost $40,000 - $50,000.It doesn't sound like a lot of money for folks from CA and NY but for our local standards it is and IMO kills the cashflow and is unnecessary overcapitalization.Each to their own I guess.Just had a call the other week with a fellow from CA that bought a few turd properties from a local scam artist and is flying to town to try and rehab them himself.Another fella I managed to save even tho he lost his deposit of $1,000 as the seller (Another known scam artist) made him commit to the deal without allowing an inspection or even a walkthrough...If that isn't a red flag then I don't know what is 🤷‍♂️Hat's off to you for flying into to town to see the property for yourself.Wishing you much success

Eventually, I’d like to get into long-term rentals (out of state) and short-term rentals (both in and out of state).Besides real estate, I’m really into outdoor activities like surfing, mountain biking, kitesurfing, snowboarding, skateboarding, and rock climbing.

If it was a primary residence, there are conventional low LTV's, and as a popular second home destination,10-15% down payments for a SFR is common for well qualified buyers.

During the pandemic years, it became increasingly popular to lease month to month which creates opportunity to increase rents rapidly on in place tenants.I'm buying a condo this month in which the tenant agreed to stay and signed a new lease raising his rent $250 per month. 

Looking at AirDNA results, my biggest concern is occupancy rates, most of the calendars I look at have large gaps in them, and when you spend close to $500/sq. ft at current prices (in STR-designated areas), your property needs to rent well above 80% or you charge crazy nightly rates.We've also seen very few property management companies that charge less than 25% there (and 25% is rare), and some STR neighborhoods require you to use their designated PM (Desert Colors only allows Red Rock, and they are at 40% commissions - ouch!).