So, if the numbers make sense to you, you need a home to live in, you can afford it no matter what the market does, it offsets what you might currently be spending on rent, or any other such factors, this could be an ideal time for you, personally, to buy.  

My ideal situation is to enter into a house hacking type of strategy.

The only true way to find the actual value of a property is to have a willing and knowledgable seller and buyer agree to close on a property.A lot of people here sound like owners I deal with that think their property is something pretty special - Like 20% above market value special.If you don't like an appraisal, go to the lender and make your case on why. 

If you advertised "Ideally I would like $1600 per month, but call me and tell me how much you can afford and we can work something out..." it would be a closer analogy and I think it could be a potential problem.  

It’s like a championship Boxing Match . it takes a few rounds for the champ to win and he may even loose a round or two ( here we are in a lost round ) but the champions get up and the knocks the dude out and brings home the golden glove .

I think the most important point I got from both of you is to not use "ideal" rents but the existing ones.

It seems to me that a hotel in the middle of or just about to start a PIP could be ideal.

Ideally, right after we get tenants in it.

Be reasonable though they are probably not going to match long term rates but if you can get to a break even or just after rents couple hundo a month.. but give you a year extension thats a good outcome..

You cannot grow that 34% once it is gone, and the effective compound interest may still make it worth keeping it in the 401k, even if withdrawing at 50%, hypothetically.There could be a clawback on unvested dollars from your employer with an early withdrawal (I don't know if this is a thing, but worth knowing before you lose match dollars).