My interest in real estate investing started from reading books and listening to podcasts, which got my thinking about exploring house hacking as my first venture.

If you were to venture into STR I would suggest starting with one to test the market and see if it is something you would like to continue to expand into. 

Combine this househacking with joint venturing on some commercial property around the same market (5-20 units) with a few other investors that compliment your skillset and viola, you will obtain 30-50 units in 3-5 years. 

We live in Ohio and both have prior real estate investing experience, but this is our first business venture working together, and would like to set up our LLC in Wyoming. 

As others have mentioned, I don't think this is a good idea since it appears that you are risking her retirement income on a venture where you have no experience in.Is her pre-tax income going to be $105,000 after retiring?

Obviously the answer I'm sure depends on a number of factors (affordability, reliability, etc.) Virtual Assistant would be less affordable but you would have a higher margin and JV partners would be possibly in many c...

If you have the cash and want to venture into buying a separate rental from your primary, I would do that over wholesaling personally. ~ Lindsey

If $200K pre-tax is realistic while doing wholesaling then I would be fully content with it, and I would scale it (I use the word in literal sense, meaning: make my operations grow ever larger, not necessarily Warren Buffett large:-)) from there by investing extra capital and using financing leverages to grow into other ventures.

Start building your network meanwhile by Meetups for Real Estate and also  Facebook Groups for Real Estate in your areaMaybe you can get into a Joint Venture with some one and that can escalate the time to buy  a property

Try a private lender  and a Joint Venture