With this option, we're wondering if it's better to offer it as a 3 bed 1.5 bath with 2 bonus rooms (which we live out of), or rework one of the rooms into an actual bedroom to make it a 4 bed.With either option, we're also wondering if it's best to have the cashflow of our current house to offset any unexpected expenses, or if we should pay extra and try to pay off our current house as soon as possible.

I have certainly added half baths to a renovation, but never a full bath without a MAJOR renovation (read: moving walls and reworking the whole flow of the house).  

I can rework the invoices on myside to include the pet fees etc... in on invoice but I lose the granularity of information and have to make notes in the payments. 

This can be good but as far as getting things done in a timely manner but in my experience it can also be bad as I feel that I am constantly being stuck with bills for shoddy service/rework.2. 

But turning a former restaurant space into a new restaurant space may cost nothing, or could need a full rework.  

And if you close the attic access door, are you able to add another without reworking the stairs, which can get very expensive quickly.

All it takes is one inspector to be perticular about the measurement, and it could cost you your entire basement, or add the cost of trying to lower the slab After you completed your remodel, which means a lot of rework...One additional bit of information related to the City of Chicago Building code which I hope will help someone in a tight situation down the road.

If I have 4 properties of my own really I have to convince IRS that I have to put 750 hrs to be considered as RE professional why not something less as every year I spend enough hrs to find tenants/screen them/coordinate with my handyman/cleaners/ HOA to manage all my properties..I am tending to believe that if I show some minimum criteria for hrs in my RE work IRS would be nice to me :)

Of course you can make RE work anywhere, but if your real goal is to retire within 30 years, using Real Estate as your vehicle.....and if you are serious about this.....then you owe it to yourself to at least consider moving to an area where Real Estate is easier.

Otherwise, you can re-stain them with a close enough color to minimize the amount of rework.