IE if you tell me "Hey, we can change the kitchen layout and rehab the bathroom for $20k", I'm going to want to know how that $20k translates to the amount of rent I'm receiving. 3.

You may also want to have the plumber do a pressure test on the gas lines (if applicable) to make sure no cracks/leaks there as well.If the structural and mechanical components check out to a reasonable level of comfort for you, then you just need to go room by room and decide if you are going to change the layout at all.  

My question is do i reinstall the old custom cabinets or take advantage of the gutted kitchen, install new cabinets with a better layout. 

It sounds like our buildings actually may be a similar layout.

I'm not sure the layout of your neighborhood, but maybe putting out a few dollars to offer up a gathering place away from your property is possible if it doesn't produce a nuisance with another neighbor.

So the city gives me two options: - make second unit smaller (up to 750 sqft as it can only be 50% of the first unit)  so that it can be a second unit- or apply for the house become a duplex.The first choice does not work for me because it would alter the whole layout of the second unit and from investment point of view it does not give me any benefit.The second choice would be very expensive as the city said it would cost about 50K for all the fees to pay for the city to legalize it.

Will lay out all the negatives: premium gas only, mileage is God awful, very expensive repair costs (even if you DIY, which I do), eats through performance summer tires, needs winter tire set-up for sure, increased insurance rates, back seat is not good if you got a kid in a carseat, or adults for long trips.Believe me, it’s not pretty at times!

It has a great layout and outdoor space, but it is small is square footage and has a tiny bedroom.

If you have non-damaged timeless materials, IMO you do not replace these unless necessary - i.e. a complete room layout change in a kitchen, removing walls, etc.

if you were an expert in that area , i would say you could do some of your own estimates , but that doesn't sound to be the case .depending on the size and layout of the units , you can add direct vent rinnai space heaters , then separate heat , thats something i have always done .