As with most people starting out - having the 20%-30% equity to put in the deal is the challenge. 

I am not the expert, but just from talking with people and seeing the posts pitches from wholesalers.

Most people know this. 

My question is what have people used with success to best track their time/investments over the year?

Join one and start volunteering - it’s the best way to network and meet like minded people.

I’m new to REI and looking forward to learning and connecting with people in the BP community!

People are losing money.

You should vet the company to ensure they have the resources to pay the rent.You ALWAYS do background checks on the people living in your property because if you let in an axe murderer and they harm someone, you are likely to get sued.Whether or not you charge an application fee is up to you.  

My question is how do most people make the jump to the 2nd STR property if you're generating $25k per year on the high end? 

My neighbor has listed his but also has had occupancy issues as an STR and said that most people looking for either rooms or cheap stays but I can't comment on that as I have no experience listing as an MTR.