(California has strict tenant laws and we will not consider a booking without one).Currently there is only street parking for the unit, which we have theorized may be a filter cutting us out of many potential bookings.

I'm completely fed up and I am trying to figure out if it's worth keeping to rent out or if I should just cut my losses and sell it. 

For example, even though it was little unit, inspector required whole unit tied fire alarm.  

What I have to work with: - An LLC (currently just run STR taxes through this)- A Type S Corp (I run my ad business through this, but will shift it over to construction)- A General Contractors license in the state of Oregon, tied to Type S Corp (have had and maintained since July of 2022)- A construction skillset. 

Basically, he is able to avoid all the bank requirements and cut out the middle-man syndication. 

Let's say 3 young single guys want to buy investment triplex.  5 years later your credit is all tied up in that triplex so when one of your partners gets married and has kids and his wife wants to buy a house for the family, they can't do it, because his name is on that investment mortgage. 

However at least in our market you have to have POF or Strong letter from your bank to get the seller to allow you to go into contract subject to entitlements.. then you need usually 50 to 100k in EM to tie it up.. then you need another 50 to 100k or more for entitlements.. then you go into contract with one of the national or regional builders and then you pray they will close on time. 

If so, does it also tie up the tenant's ability to obtain a moving permit?

Larger deals tend to trade in retail at higher cap rates.What you need to decide is how long you want your money tied up into a deal (their exit strategy), and how much you want to place, and if you get cash flow right away, partial, or none until certain metrics are hit.As an example you might get 8% preferred return but upside might be more marginal than a small retail turn around deal where exit is in 2 to 3 years and equity multiple is likely much higher for overall return.

In particular, in desirable areas, for permanent/good financing, often 25% down doesn't cut it.