I'm ready to invest another $50k or so and was considering investing out of state, small multifamilies in less desirable areas near me, or to continue investing in my comfort area.About the target property: I would classify it as an A or A- area based on what a lot of people call B and C areas around Chicago.

I'm not sure the building will still be for sale long enough for me to sell these two buildings Scenario #2I keep saving until I have enough for another downpayment on another four family and continue to rinse and repeat this for years.

I currently work as a Development Manager and continue to provide architectural feedback once requested. 

People are continuously complaining that it's hard to find deals but forget to understand the importance of creating relationships.

I am really interested in the Pittsburgh market and I know home values have been appreciating quite consistently over several years and expected to continue on the trend.

I've enjoyed reading discussions on the forums and I look forward to participating in them and continuing to learn and meet other real estate investors through the forums.

@Will Glaeser  I think it would be easiest to build experience and a track record of success in Area A and then transfer the experience and track to Area B to continue to grow your business. 

I personally think anyone with fewer than 20 units is wasting money by paying for software when a spreadsheet would do just fine.I recently tested TenantCloud (free for up to 75 units) and it has some really great features for a beginning Landlord, to include online marketing.

Preferably it would be the 4plex so that as cashflow is generated you can continue to work on the 5plex.

I continuously see new flip properties hit the market and when I check the tax records, they are purchased from sheriff sale.