This is just my opinion, and others can disagree, but when I am buying or selling the most expensive purchase I have made in my life, my preferences is to use an expert Now, as mentioned, not all agents are equal, but if you do find a very good one, they are well worth the commission

  - For purposes of trading equal or up in value (which is necessary in a 1031 to defer all taxes), the value of the property you build is purchase price at time of acquisition + cost of improvements completed before the exchange completes. 

I'm in the process of getting everything caught up for this year with hopes to hand it off in January.  2) My wife equally sucks at bookkeeping. 

@Luke MasaschiLike above advice, unfortunately, there's no calculation that says X amenity in an STR equals Y price increase. 

Ownership in property will be equal. 

What if they finally succeed in their misguided effort to "protect economic equality"?

4 base hits equal a run.

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

As a pass-through, a deduction on the property equals income for the s-corp like Jon points out. 

For instance, with a conservative estimate of 1 month of vacancy per year and 1% of the property value in annual maintenance costs, you could be looking at an additional $2,000+ in costs annually, not to mention the effort and time involved in managing these issues from afar.With all that said, real estate is worth the effort but not all deals are created equal.