(WI taxes on my corporate income, concerns from my employers perspective, etc.)Scenario 1: Request my employer mark my work location as 'Remote'. 

We are in the 2/5 years so we could sell and profit 200K+ tax free or we could rent with cash flow (not including mx) 1K/Month.

Don't forget to add an adviser to your team to work with your CPA/tax professional to maximize the tax benefits available on each and every project.

I know this isn't your problem but if you are able to move before your lease ends I will pay you $1,000, prorate your rent to the day you move and return the security deposit together with the extra thousand and prorated rent the day you give me the keys.

IRS guidelines would require you to seek out a tax professional but i believe you are taxed on gifts above $14k.

At the state level a law was proposed to place additional 15% tax (on top of local occupancy tax) on STRs.  

CA for instance has hundreds of thousands of paper lots that were created between about 1900 and 1935. these paper lots get sold at tax sale all the time and its where a lot of the land geek type of players toil. 

Those that respond “$0” or something ridiculous, you can request income documentation from them to justify.Don’t be afraid to share with them how much your property taxes & Insurance increased and that YOU cannot afford to absorb them.ALWAYS get an increase or something of value annually or tenants will start thinking they should never have an increase, making future increases that much more difficult to negotiate.

Due to taxes, the up and down nature of stocks and also out of a desire to actually own something real and tangible, I decided to invest in real estate.

And the property assessment would need to be changed, and of course, taxes increased, as well as separate utilities.