I would base my decision to buy more on my investing goals, am I buying for cash flow, appreciation, or tax savings.

I attempted to do taxes (married, filing jointly with my spouse) on turbo-tax.

You will get your own financing quotes, your own real estate taxes, and your own insurance quotes.  

In general, travel for business(education, networking) is deductible if you are already in a trade or business(I.E. have a rental, flip).There are unique rules to deduct foreign travel costs.attendees may have a more difficult time writing off the cost of the trip if they add significant vacation days(no business) before or after the trip.However, you can plan properly to make the trip 100% deductible.

Hey Ralph,Typically if you sell a property or any asset for a gain within 12 months, you pay capital gains tax at your tax rate. 

Is this a Single Family Rental - it can work for sure to start with negative cash flow - but this is a very very risky strategy - especially if there aren't other considerations like tax benefits on a larger portfolio or anything else I'm missing

Consider factors like potential tax implications and long-term financial benefits before making a decision.

As I was preparing my taxes, my tax professional advised me that management LLC is redundancy and it doesn't make sense to have, it's like moving my money from one pocket to the other.

If you know you want to get into STRs, find properties in your market or market of interest that are managed by Vacasa and Evolve that are underperforming and have guest feedback indicating the the customer service from the host was poor (as it usually is with the big national STR PMs), look up the owner's name on the county or city tax records, and cold call or text them.

You should leverage the paid off property that you have by doing a cash out refinance and then use that to buy a new build for $300-350k putting at least 25-30% down, you can find these that will rent for 7% (annual) of the purchase price and have very low property taxes and insurance.