Offering money is only going to prolong the process. 

If you signed again and it's another year lease then you prolonged your time dealing with this tenant.

A prolonged vacancy is why you allow for vacancy in your pre purchase due dilligance.

Here's a wild idea - an prolonged closing.

If you don't handle all the paperwork correctly and serve notices at the right time and in the right manner, you will prolong the whole process.  

Do not wait any longer it will just prolong the inevitable.  

We will people with foreclosures that went a short period of time (6 - 9 months) if they have a clean credit report for the past 2 years.We will never take tenants with any evictions or if they ever forced a prolonged foreclosure as 1) They have tasted what it is like to live rent/mortgage free and they just might like the taste of that  2) They probably know all of the loopholes and stall tactics in the book as well as every obscure right they have.Pass on them.

While most of these homes bought during the recession have been foreclosed on, there are ways to prolong this process in my state so somebody can be delinquent for years before they get foreclosed on.

To determine if the expense should be classified as a capital improvement or a deductible repair, the context of the expense is very important.An example is, if an item of expenditure is part of a general plan of modernization, renovation or rehabilitation to equipment or other business property, it typically must be capitalized even though on its own it would be currently deductible.According to IRS Code, expenses that you must capitalize are those that:Materially increase valueSubstantially prolong useful life (including replacement of deteriorating assets)Adapt the property to a new or different useHowever, you are allowed to deduct expenses and fees for routine maintenance and repairs that help keep the property in efficient operating condition.

@Connie Chan if you’re talking in general for me it’s probably maintenance that I haven’t encountered before (which is becoming less and less) or pro longed vacancy.If you’re talking remote investing (which I’ve also done), then that adds a whole new ball game.I’d say getting ripped off by contractors would be number 1 then, or overpaying for stuff (which happens all the time, mainly to people from the west coast).