From the sentiment of your post it seems like you're viewing the buyers as strictly investors when they may lean more towards traditional homeowners looking for a quality of life improvement or an improvement on their current financial situation today.Let's say the buyer pays 465k and has a 5% interest rate.

Strictly advice to move forward in these ventures.Your attitude may be the best thing about your ability going forward. 

I know that i could buy my next multi family property as a primary residence close by move in, rent half live in the other and than rent where i am now which would cash flow upwards of 1k monthly, or i could buy another multi as strictly an investment property out of state which would be a lot cheaper (taxes and cost of property) and a lot more landlord friendly laws than New York, i guess i’m just undecided on which route i want to take and I’m trying to weigh the pros and cons of each scenario.

What I mean is, some investors look strictly at cash on cash return, some look at cap rate, others just want to make sure their mortgage is covered.

But I find from personal experience and from my buyers' Airbnb experience that it's a bit of a hassle trying to get guests to rebook at the new listing.I don't know how strict Joshue Tree is at enforcement, but in Denver and Colorado Springs here, you could probably get away with an STR listing for three months without the license.

bad tenants need to be strictly held to the lease or the will try to take advantage of landlord softness. 

Don't use it strictly as a tool to turn the property into one you want to live in. 

The town of Shandaken has some pretty strict rules regarding STRs, requiring a "absent owner" STR to be owned for a year before it can be used as an STR, and also limiting the number of STRs to 100 properties.

We’re being funny because there's still a bit of nuance here.There are strict guidelines and it's sometimes a blurry line between being an RE pro vs not.

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