Every time a guru “education” course was co pleated, I’d receive 10 -20 phone calls from either investor wannabes “building their team” in preparation for all the real estate “great” deals they were going to uncover or the same wannabes who had already identified a “great” deal (they hadn’t submitted let alone secured acceptance of an offer yet) and were lining up their financing which since they were purchasing at 50% of the value they’d end up with not only 100% financing but also walk away from the closing table with cash in their pocket.  

I think that is always recommended and it is something I do.My inspector has uncovered things they werent aware of and has also alerted me to issues to monitor to make sure they are rehabbed properly (for instance ensuring that the electrical scope included adding additional circuits because the current number was deficient).

I wouldn't touch your 1st mortgage unless the blended rate (Both the 1st and 2nd Position loan rate) is higher than a traditional cash out refi. 

Issues can and will be uncovered once a renovation gets going. 

If you want to blend a home with 3 rentals then you are likely to end up with a 4 plex that does not cash flow in the same way as it would have if all the units were rentals.

Old West End might be a spot to explore for this blend, but it's essential to do your due diligence.If you need any advice on financing options for these investments, I'm happy to help!

A visual inspection and a pressure test should uncover most issues. 

But my personal answer is to BRRRR, it's a great blend of both Flipping and Buy and Hold.

I disregard those and focus on comps that have a realistic looking calendar where there's a blend of available and booked dates.

I think your best option is to do some kind of blended portfolio into real estate.