As you will be living on the property, any concern about securing retroactive permits for the work can be deferred until such time as you decide to sell or rent.    

The key is the way you package your application but without an understanding of a lender's guidelines, it can be tricky to present your app in the best light. 

@Nick Gee Your best bet to avoid or defer capital gains would be to use a 1031 Exchange to invest in a new property.

The best time to buy is always the present you'll be 80 years old waiting for the right time.

Since you are in your 40s you probably know a lot of people who had a career, then switched jobs, which means they probably have an IRA they can convert into a self directed IRA which they could loan to you and make money tax deferred.

This presents a situation where were looking for a niche tenant - someone who can afford to buy a home but has life circumstances leading them to rent and who also does only minimum cooking or eats out a lot.

@Michael Scarpa that area is old Mill towns which will not appreciate and will have a good chance for deferred maintenance issues.

I don't deal with Booking.com or an individual website.We were presented with an off-market offer recently for $940,000.

Prior to the purchase of this house, I owned a home in Truckee, CA that I purchased in 2016 for $385k and sold in late 2020 for $600k.Occupancy: Will be owner-occupied.Value of property at present and/or your offer: Property was purchased for $140k in March.

If you follow this path you'll get some money tax free and the rest tax deferred into a better rental for you - A very good scenario.