My CPA was unsure... do you issue 1090-NEC for the difference between 1099-K and 1099-MISC or do you double up the income (i.e. 1099-NEC for gross rents from PM, 1099-K of the net owner distribution on 1099-K, then owner reports double income and puts a line item expense for the 1099-K since 1099-MISC covers gross rents).You need a new accountant lolPM issues 1099-MISC, not NEC for rental income paid to property owners.You would still issue the rental income paid to the owners regardless of the payment method.The Property Owners should add an expense line item on Schedule C stating that income reported twice on Form 1099 to offset any duplicated amount.

Then there’s city regulations—some places heavily restrict short-term rentals, so you’ve got to check the rules.If you find the right spot and automate stuff (guest communication, cleaning, etc.), it can be profitable.

So, comps can help with figuring out local cap rates, then you need the income from the property to determine a value.

If you are syndicating or partnering with other investors to fund a Sponsor's deal and you are a company doing this (LLC, partnership) then get a PPM attorney and file with the SEC. 506B is easiest but if it is really risky...then 506C is best. 

investors can figure on 10 to 12% return on PMLs   generally they are short term 6 months to 18 months.. in my 40 plus years at PML I find most investors started as landlords then tire of it and start to diversify.

They asked me to empty my savings, max out cards and then finally to take out a loan.

Feel free to reach out and if not then good look furthermore

If it is last rental rate charged, then you may have to get creative to accomplish what you want to while still working within the law.Here's an idea to explore.....If it is a 10% increase over the last rental rate you charged, consider using a step pricing lease if allowed by your state. 

Then you can read a more in-depth book like The Book On Rental Property Investing by Brandon Turner or The Unofficial Guide to Real Estate Investing by Spencer Strauss.2.

Man, Bed-Stuy was rough then.