Even though ALOT and I mean ALOT of people on bigger pockets or friends and family have told me airnbnb arbitrage wouldn't work out I have been pretty successful even though I was pretty much self learnt without any form of joining a course or anything like that.

Yes, 401(k) plans, IRAs, SEP-IRAs and all other kinds of retirement plans are still the backbone of your wealth accumulation, especially if they are self-directed.

We have the means to self fund two to four properties off the bat. 

Over the past 6 months I have been really researching and devoting myself to self improvement and learning.

I’m self managing myself but the tax side of it is a little confusing to me but I’m recording everything involved as far as maintenance, traveling, expenses etc. just want to know what some people would do in my situation or what to I can benefit from come tax season  @Angelo LlamasI recommend that you find a real estate accountant to help you understand and prepare your taxes.Bigger Pockets is a great place to find a real estate tax accountant. 

Quote from @Maria Jeanette: I am considering using Equity Trust to set up a self-directed IRA to purchase properties.

You cannot go after them as for a regulation a+ offering is self attestation (meaning you are attesting that you are not putting in more than 10%).

What I would tell you is that as we built our portfolio we continued working our full time corporate (cubicle) jobs until we had 20 units (self-managing them along the way).

If you’re self managing and personally moving and wish to keep self managing in your new location. 

We (my wife and I) have been at it for a few years - self managing mid and short term rentals.