The bigger the list, the better chance they can sell their listing.

Wholesalers can bring you properties before they hit the MLS, which might give you a better chance at finding something with the right numbers.

It is vey risky and chances are you will lose money if you don't know what you are doing. 

Is there a chance they could catch up over time?

Even if you purchased the investment property first, at least you would have the cash flow & equity of your investment property (wouldn't recommend purchasing at market value in this market) to improve your financial profile and increase your chances of being qualified for a primary residence loan, instead of the other way around.

Additionally, strong credit, a solid track record in similar projects, and a well-detailed plan for the rehab can also improve your chances of securing favorable financing terms.

Explain you probably won’t get a tenant for next month but you’re willing to take a chance on October.

There's a very good chance the issue(s) you face have already been discussed and answered.Ask questions in the appropriate forum.

It reduces risk by having them know the laws which are extensive (down to needing a compliant monthly statement) etc.The other component is no chance I could do it for that price either.

@Brian Batista yes, your best chances of finding good title companies in your area that have experience at subject to transactions are through other investors that have done subject to transactions with those title companies in your area.