You definitely wont get an app like that for free, so how much would you be willing to pay to a company to submit it for you, vs spending 10 minutes once a month to submit taxes? 

@Donnie Jones I agree with Jonathan and Nathan, its definitely a challenge to start off wholesaling and takes a lot of grit and consistency to see success but not impossible.

I'll definitely check out Set For Life by Scott Trench and The Total Money Makeover by Dave Ramsey for more financial insights.Watching BiggerPockets podcasts and networking with local investors are great suggestions.

Well, I'm not ultra wealthy - I'm not even sure if I fit the definition of wealthy - but I guess I'll chime in anyway.

It is definitely a bit more tricky on an investment property, but it can for sure be done.What area of Chicago is the property in?

@Michael BaumEvery property we ever stayed at had a physical book so yes - it definitely suffices.

Definitely on market.2) This is such a tough question to answer, but I think it might be something along the lines of don't overleverage.

And you definitely do not need a license to be an investor.

@Sam RobbinsYou definitely can't do an STR with an HPR.

The Lake Tahoe market has many intricacies regarding short-term rentals, but navigating them is definitely possible.