Lenders are almost universal in their requirement that a borrower has "skin in the game".

Based on your information, it may appear no2) The second question is whether the property will generate positive rental income over a 3-5 year period, after normal depreciation.If it is, and it is significant, it may be worthwhile to get a cost segregation.

Fixer upper MFH could be low in inventory but normal ones are still there

Sure, I cover the water to refill it, but my water bills tend to be pretty "normal" so it doesn't seem to be costing me a ton of extra $$.Point is - yes, this is completely normal and it's something your cleaners should be doing at every turn. 

Sections of highway will be closed for a good amount of time.I have seen many reports that the area is very crowed with is normal for this time of year.

We could not respond in a normal time frame that we usually respond in.So just wondering if guests were trying to contact hosts to find out if their rental was still available etc.. and not getting responses and guests were getting panicky.  

Which is basically just reported on your schedule E/C and taxed just as normal.  

Any small damages by the tenant he will make the owner pay for it and claim it’s normal wear and tear when it’s clearly the tenants fault.

Its to make sure you have enough skin in the game on this property such that when you buy the next one you're not going to be in over your ski's.Hope that helps, there are many ways to structure your situation so that you can bob and weave around these obstacles.

I prefer the cleaners coming closer to the time of the next guest than immediately after the last guest leaves (normally this is only an issue during our slower season).