You go somewhere like Stamford, Norwalk, Fairfield county, etc. you will pay more/less cash flow but higher rents with higher income professionals being so close to NYC. 

It also gives the tenant time to arrange for 1st month's rent, if they choose to not pay it along with the security deposit. 

If managed by the owner currently and you plan to hire people add in a 30% loss of revenue.  

First thing you should do is go the the planning department of your city to find out if your zoning supports what your trying to do

What we have found is that large occupancy events are typically planned months in advance.  

It might help pay for your expenses if you house hack but I bet the number of markets a 3.5% down payment is cash flowing has shrunk significantly over the past 2 years.

Now, I want to pay it forward by creating a step-by-step real estate investing course specifically for high-earning professionals who might be feeling the same pressures I once did.I know how tough it can be to juggle a demanding career and personal life while trying to invest wisely.

The plan is to cease the STR next year and switch to a MTR and thus, I would then report that property on Schedule E.My other property, which was also recently acquired, is already a MTR, and I would need to report it on Schedule E.So my question is: can I report one property on SCH E and the other on SCH C even though they are both owned by one LLC?

I’m currently in California but I plan on traveling to Florida sometime in the next week or so to check things out.

I would recommend keeping it on if you plan to move into it (ideally immediately so you can keep the prop tax discount)  or if it has sentimental value.