Have also recently heard from a lender that it needs to be a double-wide and built after a certain date for them to lend on it so may want to check that out as well.

those rules are totally out dated.. they were fine coming out of the GFC  but values have risen faster than rent.. not that you cant get those today you can if your willing to risk asset class and or you hunt for these on your own direct to seller.

The listing says, “calling all rehabbers… best offer by such date”.

I will be somewhat tough if you don't buy soon as the holiday bookings will make it difficult to transition, get inspections and closing dates to coincide with very tight windows and also the possibility of cancelling existing reservations for people that have big holiday bookings.Depending on what type of property you are looking at will make big difference also.

However, when the lease expires in 5 years, if the tenant were to leave, I don't know how long we'd have to wait to get a new tenant, how much renovating the space for the new tenant might cost etc.

Find a realtor who is willing to take the time to educate you, you set the expectations and who knows, the realtor may have an old / expired listing - voila!

Side note, I hope it does not reach the summary process, but this tenant is particularly combative and has also blocked my number...The verbiage on the NTQ isANY SUMS OF MONEY TENDERED TO LANDLORD OR THEIR ATTORNEY AFTER THE DATE OF THIS NOTICE SHALL BE ACCEPTED AS PAYMENT FOR USE AND OCCUPANCY AND COSTS OF EVICTION ONLY, AND SHALL NOT BE CONSIDERED ACCEPTANCE OF RENT, NOR SHALL IT PREJUDICE OR PREVENT THE LANDLORD FROM PURSUING SUCH REMEDIES, INCLUDING EVICTION, TO WHICH IT MAY BE ENTITLED AT LAW OR IN EQUITY.Best, Michael 

My thought process is to see the rent rate for other homes near the area, see which house profits more after mortgage, figure out the average pay-off date, and go from there.Sorry in advance if this post is a little messy, if anyone can point me to an article or provide insight on what strategy works best please let me know!

Is there different tax bracket if I sell it within 6 months of purchase than after 6 months of purchase date?

The current date reflects that who is buying right now, are people under 40 years of age.