@Mark S.In my 20+ years of working exclusively with investors and representing clients before the IRS, I have never seen the IRS raising an issue about 1099s for Schedule E landlords - despite the fact that the form itself has a specific checkbox.Also, there were proposed rules a few years ago that specifically required 1099s from landlords - which sort of hints that the IRS did not consider them mandatory without the new rules.

@Dale E.

It would serve you better to ask for prior years Schedule E to get a good idea of what the past has done and you create your own pro forma based upon your numbers of what improvements, cap ex, and raise in rent could do for the property.

@Christian Espana Northern WI is generally STR-friendly since cabin rentals are incredibly popular in these areas but always double check with the city/county.

Like I said, it's not popular around here but it is a good way to test it out.

@Michael Sontheimer-  most  lenders will use your  the  scehdule E  from your  tax returns for the past  2 yrs  to determine the   rental income that is usable for  qualifying for a loan ....so  if you have the ability to make this  schdule as  healthy as possible  - you might  consider this  ....if the  rentals  have been owned for under a year - the lenders  may use 75% of the  lease  amount  

Feel free to reach out to me and I’ll send you a free copy of my e-book on multi family investing if you think it would help.

Quote from @Scott E.: KyleHere is what you are going to have for out of pocket expenses:  -DOWN PAYMENT: 25% of the purchase price  -REMODEL: Cost to renovate property, if applicable.

Quote from @Bob E.: ….I would approach to buyer about refinancing you out of the property.  

So if you have a rental property, you can report via Schedule E even if you don't have an LLC.