Hi Seth, I'd be happy to hop on a call and go over some basics with you.

This gets a little wonky, but the IRS is going to look at that future sale and allocate the built up capital gain pro rata  between the amount of time it was a primary residence vs the amount of time it was a rental. 

@Giles D.You may actually owe the IRS money if they claimed bonus depreciation.

(IRS provides tables to calculate the amount(s) based on your life expectancy each year.) 

My thoughts: East Bay:- Close to a BART station to traveling medical worker/corporate person could hop on a bus/BART to work: El Cerrito, San Leandro, Hayward, Fremont, Walnut Creek, Pleasant Hill, Concord, Dublin, Pleasanton- Maybe Richmond, Antioch and Pittsburg but some parts have a lot of crime. - Going further out Brentwood and Oakley have appreciated quite a bit and have pretty good schools- Something with potential to add value: ADU attached to the main house or separately in the backyard in the future to get additional rent.

Well, when it comes to filing taxes I usually don't rely on the kindness of strangers (especially when they have no liability), but if you think getting a lot of replies (some conflicting) will help you make up your mind - Have at it.Honestly, am not trying to be a jerk (as you can see it comes naturally), but your tax guy is the best liability shield against the IRS you have. 

As for a W-9, that is required if you're reporting to the IRS that company/person's earnings and technically is required for anything paid over $600 (I believe) to a single person/entity in a given year so you can issue a 1099.

Hi Nicholas,When thinking about taxes and deductions for your real estate business, according to the last IRS info I saw, you cannot deduct improvements or upgrades.  

Hi Natalie, My husband is content to listen to my goals and okay with me using our mutual funds to acquire our first property, he was even okay with me continuing on this path after my first attempt at a duplex house hack fell through leaving us apartment hopping.

In addition, the 1031 like-kind exchange allows investors to defer taxes when they reinvest the proceeds from the sale of an investment property into another investment property.Plus the withholding 15% tax is refundable once a tax report is produced and the capital gains are submitted to the IRS.