You could do all in one or all in separate LLC within series LLC.

If some or all of the income is considered to be earned income, such as for management services, then that would qualify as self-employment income capable of being used to sponsor a Solo 401(k) and make contributions.

Can you use any or all of what you learned? 

In addition you learned what is a good value, what causes PM headaches (inadequate parking to me is a immediate red flag), how to do certain repairs and have a trusted contractor list, know how to market the property and find good tenants, know how to track rent and expenses, and most importantly what you like about RE investing and what you do not like (maybe you learn house hacking is not for you or that you do not like dealing with tenants).  

Good luck and don't let that fear or all the "what ifs" hold you back!

Feel free to answer one, some or all of the questions: P.

So I get most or all of my money back out.2.

Because this would be an investment property from day 1, you will likely need 20% - 25% down.To minimize your cash out of pocket, you can negotiate that the seller pay part or all of the closing costs.

@Paul Defngin - I know from listening to podcasts here on BP that they use the term house hacking to mean renting out part of your primary residence so that it pays for most or all of your mortgage.

I have also attempted to reach out to private lenders I have found on this site but they tell me they "don't invest in ny", "only invest in their area", or all of their funds have been lent out at the moment.