Hey TY, I only do off-market DTS, but I would recommend partnering at first with an experienced on-market wholesaler or a fix-and-flip investor so you can have better credentials when submitting an offer. 

As he technically didn't, but I kind of read in-between the lines.My question is: Where can I be better for a coach to see the benefit in training me.

Make super aggressive offers with a low success rate but focus on volume and gathering key data about seller motivation to better increase chances of success. 5.

Seeing the situation, is my plan the best way to move foreward or does anyone have a better way?

You are better off exchanging into an SFR, multifamily or DST investment depending on how much you have to invest. 

Do you want more doors, more money, or a better path to eventual time freedom?

You can get a better return on that dollar by updating the roof.To paraphrase Morgen Housel; at the end of the day it really needs to pass the sleep test.

Call and ask them to email you the terms before you pay for an appraisal and get a better understanding of who they are and what they do.      

@Sharon Zhou without a better understanding of the tenant's plans, the answer is NO!

We are thinking that we can trade the amount of effort that we are putting into the C class properties for self managing STR and significantly increase our cashflow while buying in a better class (more appreciation upside).