But they all have a longer window (especially the TIC and NNN which can commonly be found with 20 year lease terms).  

This will be most of the house since I'll only be using the small bedroom, tenants will be in the other rooms + the common areas.Questions:1) I can deduct the full costs of furniture used to furnish the rooms and common areas, yes?

Delinquent HOA assessment not paid by the foreclosed owner is a common problem that becomes the burden of the new Buyer, who has to settle with the HOA.Do the (sometimes) excessive HOA back dues increase the Cost Basis of the property that can be written off against ordinary gains or does it expense out (as passive income) on IRS Schedule E?

They have a maintenance guy that handles anything so our contact with the landlord is very limited.I would love to this property as my first investment property, however, I'm having trouble thinking about how I to be going about this.My initial thoughts are to just put out a feeler saying how much my wife and I love this area and that we eventually would like to hopefully buy some day and just politely ask that if they were ever thinking of it, to please keep us in mind.I'm having trouble figuring out how to communicate this message.

It gives you a low barrier of entry to buying (low down payment), you get favorable loan terms, it eases you into property management and lets you manage maintenance issues (hiring or DIY).There are lots of great videos and webinars on BP that go through this process in detail.Welcome to BP!

Furthermore, in these types of neighborhoods, you will keep having maintenance issues.

@Greg Scott, I should have mentioned that window units are really common in my city. 

I can send you to them, however.So you have the common question of buying properties in your own name or taking title in an entity. 

I mean, I know what the MA gov website recommends but is it actually common practice to spend that kind of money on every rental property you purchase that has lead in it?

Multiple offer situation is common.