As we are not seating on an un-limited cash pile, a few winning TS bids would dry up our fund. 

@Caroline Hires Just a thought, from an online marketing perspective, I googled "how to invest 100k" and didn't see any top-of-page advertisers - you might bid on that keyword (or similar), create a short landing page making the case for why investing in real estate with you is a good idea, and how to contact you to chat at the local Starbucks.

Find a local small contractor that specializes in water damage and get them to bid the project making it crystal clear that it's you paying and not the fat wallet insurance company.

Bid $10-15k more than a cash buyer.

I was planning to give multiple bids like 70K in cash and quick closing or 100k with conventional mortgage.

Contemplating a bid of $55k. 

The agent told me he's waiting for a contractor to give him a bid for repairs so he can verify what I'm saying it needs and what it's going to cost.

In my area, roof bids are usually around $300-320 per square.  

My brother in law and I have been trying to purchase a rental for a few months now but we have been having trouble getting bids accepted.A few days ago we put in a bid on a short sale house last Friday.  

There are  many people there bidding on one thing but out of courtesy to the auctioneer and seller who's forum you are using, wait until they are done.