This isn't overly complicated, but it does take conscious effort to make sure everything is handled correctly, every time.  

It does get a bit more complicated and I end up showing that the rentals are occupied and in some times the lease agreements so they can see the rental as an asset rather than a liability (e.g. if it is expected to be generating income for me).The biggest thing from my POV that makes it easy to get a loan is the income history from my W2 job. 

My suggestion would be to just pretend you're renting out the unit as well, it will keep your relationship with your tenants much less complicated.

His business has suffered due to the pandemic and the lack of demand for his services.2 weeks ago he asked me that he would like to extend his lease for another year; the lease does not expire until the end of May (30 days notice). knowing the difficulties he starts to have with rent payments and the line of business he is in, i don't expect his financial situation to improve anytime soon.In order to avoid an eventual non payment of rent and eviction procedure (complicated during Covid), I was thinking about doing a month to month lease instead of a term lease.

Sec. 93.053 also states the burden of proof is on the tenant in a judicial action to enforce their rights. 

It turns out is was a pretty good buy, however, given the housing laws in Portland that are complicated and burdensome I don't think I'll be buying here again. 

This transaction is complicated as the lender was sued by the owner and was forced to buy the property back from her.  

We are trying to learn the nuances of CRE, as it seems a bit more complicated than the single family investment we are used to.  

But as a new 1099 Contractor I know that Taxes and understanding them has become much more complicated.

My agent’s advice was to lock in the off market and do the IP if I can swing it, both for the lower interest rate and contractually a Subject To will be more complicated, (we’d have to set up a trust.)