I would recommend an STR for the best tax benefits and cash flow no doubt.

a lot of people will poo poo this, but I also live in a market where cash flow is low, property taxes are high and properties are expensive (which is a relative term).

My biggest conundrum now is I want to be my own GC because even when I play with smaller numbers they’re still out of reach for me to be able to attain this goal and afford the monthly mortgage with taxes and insurance.

These special taxes, as they are called, are collected the same way as general taxes (December & May) but are listed out separately.

The units are all currently occupied right now, so we won't have to worry about the buyer's market right now haha.With the cash flow I will receive, it will be enough to take care of property taxes, insurance, and enough to save up for any emergiences with the unit that I will need to take care of, so no need to worry, I got you :)!

David,Yes, investing out of state can be a wise choice especially if you live in a State like CA, NY, NJ, CT where home prices are over priced and taxes are brutally high.

If you think you can manage a mortgage, taxes, insurance and the upkeep of a home while paying your student loans then buying is not  bad idea but if you think you will overstretch yourself renting is nto bad either.

In addition due to prop 13, the tax base is a fraction of if it sold today.   

You are looking at the rent of $2,000 and mortgage (Loan, Insurance, and Taxes) of $18000 and thinking you have $200 cash-flow.

Real estate investment can be incredibly rewarding, between the cashflow, appreciation, and tax benefits, it truly is the greatest wealth creation tool.