If that is the case be very careful that your HELOC  (with interest payments) will be paid with the rent from the new property  by a healthy amount to help for tenant turnover and repairs. 

Please click on the links, give them a read, and share your thoughts in the comments.First is a post that I feel will help not get overwhelmed with the amount of info that is here on BP:https://www.biggerpockets.com/blogs/5868/52761-the-simple-guide-to-getting-started-on-bp The second is a post that will help get you focused with your real estate investing goals:https://www.biggerpockets.com/blogs/5868/52743-im-new-to-bp-any-advice-would-be-appriciatedThe last one is a post that will help you choose an “investor friendly” real estate agent.

I am asking from a landlord perspective for damages exceeding the amount of collected security deposit where there is a low likelihood of collection directly from the tenant through a judgement.

Get quotes for all of the repairs from professionals and then send them to the seller and ask for that amount to be taken off the sales price.

Even if I could pull the full amount for windows and siding that wouldnt make sense to use that would it?

If the property is generating a good amount of cash and you're happy with it I wouldn't make a big deal about the furnace and water heater - especially if the seller is covering the roof. 

If you can stay with family, they may pay them a per day amount instead of paying for a hotel.

I got lucky buying a foreclosure which I sold for a stupid amount and put into a duplex.

Hi BP,I've been following BP for a long time and my wife and I, finally, took the plunge and bought our first rental and now our second and couldn't have done it without the huge amount of great advice from this community. 

It has been on the market for 134 days, so I may be able to negotiate a lower price if the seller is motivated.My down payment is 3%, and closing costs will be factored into the mortgage.The amount for principal, interest, property taxes, insurance, and mortgage insurance is around $740-$760/month.