Of course there are many different variables and personal preferences definitely play a major part. 

I only play in the "kiddie pool".  

Currently under contract for a large off-market residential property.Quick details: 4,200+ sqft 12bed / 5bath (2 kitchens) (No a flood zone)(Light - Medium rehab / rent-by-the-room play)My partner has been a PM in this community for 20+ years and is highly confident in this deal (as am I).The current issue is, we aren't confident the property can close with a bank due to a few seller complications.( ^Very long story, but if you want to hear it I will tell you haha)We're looking to over-raise about $335k ($255k purchase and $80k for the rehab).But we (and our contractors) know the rehab portion will come in a bit lower.Can anyone point me in the right direction?

Depending on how big the church is and how many people attend will likely play the biggest impact on how much you’re affected.

I am playing with the idea of asking them to create a monthly vacancy rate for my properties as part of THEIR job. 

this is really were good insurance comes to play. you need good insurance if you have substantial assets to protect..

Ventilation in attic plays a big role.

I'd argue that both HELOCs and CES have good utilization for both short/long term plays.

If you pay back all the upfront capital needed to fund the deal, the return becomes infinite after that, so that plays heavy.  

Pretty much all that have been mentioned here between the two vehicles.a lot of the other items come into play based on your own specific financial situation.so for what you have provided that is all