I appreciate the info though and I can deal with harsh I rather hear the truth and take it for what it is worth then to be lied to or have things sugar coated.

Do you think your unlicenced, uninsured, amateur would have paid rent when the units could not be rented as an STR.Your "tenant", the person arbitraging, during COVID could potentially not pay claiming COVID impact (and they would not be lying as COVID reduced their STR income) and could potentially be protected from COVID anti-eviction moratoriums.Our market recently passed a STR quota. 

The frequency and substantiality of sales are highly probative on the issue of holding purpose because the presence of frequent sales ordinarily belies the contention that property is being held "for investment" rather than "for sale."

This is important to know but can be lied about very easily.

This is important to know but can be lied about very easily.

I wouldn't agree to this as the seller because most likely you'll be in second position with someone who may be lying to the bank on their 1st position loan. 

This is important to know but can be lied about very easily.

However, I've recently bought a property which will likely be my last acquisition for the foreseeable future (i may be lying to myself about this, of course), so the access to loans is not a huge benefit at the moment.The job doesn't pay very well. 

But still, keep in mind your essential liberty when trading it over for promises of security that appear to be lies and false hopes thus far.

I know I can make it work and I'm good with numbers and not letting emotions get me when looking at a place (though a good historic house does tug my heartstrings), but I'd be lying if I didn't admit that I'm nervous about still making a big mistake on my first house and all the "unknowns" of real estate that are only gained with experience.