All rents are below market value and we think we can get another $2-300/unit on 2/3 units.

Doesn't sound like they are truly generating value for you then.

  - If I understand that correctly, then I wonder if the increase value offsets the cost paid out to split the parcels up.One last thought would  whether there are any underlying benefits to keeping it as one parcel, such as city regulations, etc.- I had a conversation once in my owner's rep day job about new construction of a commercial building on its own parcel adjacent to another parcel owned by the same owner. 

im sure you will find a lot of value in these forums

I think you equally partially answered that question, telling the difficulties you are facing with STR regulations.this is my prescription and what I have decided to do .consider HELOC your current property, use the money to 1- add some value to your current home if room provide ( not to exceed X $ amount) you can then rent out the extra created meat to help pay HELOC2- Use the balance of HELOC to purchase another home in an appreciating market and if possible one that allows STR. use cash flow from new property still towards HELOC and just allow second home appreciate OR if you can fine a fixer upper to do BRRRR tat will even be better.that is what I have resolved to to. you can get back to me at 301-256-1578 so we can continue to brainstorm.little cent

(My mortgage does allow it)- Does transferring the property bring any capital gains into effect due to the rise in value?

You will only see what you want to see (good deal) and not what you should see (the basement, the issues, the block values).

The market already always could list at $1 co-op but very few actually did that, sellers also could always list with flat fee $500 MLS agents but most know the value of good agents and rarely did that.

Run the numbers and think if sacrificing $600/month is worth all of the value of owning another home.

i think Arbitrage used to be a good vehicle. nowadays, people are more knowledgeable about properties, usage and values and you will have a hard time finding a desirable property at a low cost rent enough to make a profit.