I really like how strategic you were in gathering data, and organized.

Because the programs can't interpret, think, or strategize, I would try some of the old fashioned pencil, paper, worksheet, forms, booklets, and back ground reading (e.g., jk lasser has some decent rental property sale info and  Fishman's Nolo has some basics to accompany the IRS info)..

Here is my take for what its worth:City is being well managed with an active strategic plan involving the arts and the "hipster environment" and there are a few encouraging trends within the overall picture specific to Pittsfield.

He/she has bigger decisions to make in regards to growing the business and making strategic expansions.

@Daniel ReyesProperty Management: Managing the personnel and day to day decisions required to run the business side of real property ownershipAsset Management: Managing the positioning, rehab, upgrade, strategic decisions of the property to maximize long term profitPortfolio Management: Managing the strategic and decision making process in regards to the real property portfolIo as a whole, I.e., types of property to include in the portfolio, price to buy, when to sell, leverage, risk management.

Brandon Arnett Anything that takes cashflow out of your pocket as an investor is annoying: vacancy, maintenance & repair calls, cap ex, tenant turnover costs, tax & insurance increases, evictions, etc.What you might consider as “headaches” would be extended vacancy, inherited tenants, excessive maintenance calls, late rent, mold, pest inhabitation, insurance claims, tenant turnover process, eviction process, non-responsive property managers, and the list can go on.You can get ahead of most of these issues by buying properties in B- or better areas, having a thorough inspection done, doing a strategic rehab prior to placing a tenant, selecting proper insurance coverage, hiring the right property manager, and then staying in regular communication with that property manager.

Just curious if anyone has any input on the Memphis 3.0 strategic plan. 

Often, some strategic upgrades can really pay off. 

You want to be sure the lender you choose has navigated them before.Can help you strategize the lending piece for this purchase AND purchases in the futureIs an investor themselvesIf you’d like a recommendation for a lender DM me.

It gets ahead of so many potential issues and lets you do some strategic planning for what's next.)