@Stephen KunenProviding substantial services to your hosts provide suggestions that you should report it as schedule C as opposed to schedule E.Substantial services include but not limited toConcierge, meals, housekeeping, cleaning, entertainment etc.A pro of reporting it on schedule C is that losses are deductible and not subject to passive activity rulesA con is that income will also be subject to self-employment taxes in addition to income taxes.

You want to try your best to target those sellers and seek them out.

Although, it seems like a lot of effort to only make $500 or so bucks a month on a rental, well, at least if you consider that it's a much more active affair than buy/hold REI. 

We have a pretty active community in Raleigh.What makes you want to sell your townhome if its cashflowing well? 

I would also seek legal counsel in the same area where your property is to find out how you can minimize your fines.

The ones who are active in the local market should also be able to provide recommendations for contractors.

The city I'm investing is very political so I knew I needed to seek out the architect and attorney who in this case do about 95% of all of the submissions in the city and get most applications past. 

I don't spend much time on Forums, but my nephew has recommended Biggerpockets to me as a real estate agent who would like to experiment more actively with investment.

The only problem is that you will now have a payment against it if you spend it (which you would on the down payment for property #2) and you will have difficulty (I think) refinancing property #1 in the future with a active HELOC on it.

Evenings and weekends is when there's the most activity in real estate.