Zach,In my Timber experience 50 acres of harvestable timber, middle aged with healthy pine/fir trees may only come out to be a 50/50 split with whoever cuts them.

Is there any way I can restructure to lock it in and use it to temporarily augment my emergency maintenance fund until I can get it to a healthy level with rents.

If you are so busy that you don't have any time for anyone else but yourself, your long-term relationships will suffer and it's usually not healthy.

. - Is there a healthy rental market for both Houses and Apts.?

And for a healthy opposing opinion on why yellow letters may not be for everyone, I highly recommend this blog post by yet another fellow BPer:https://www.themightyinvestor.com/2016/12/24/those-friggin-yellow-letters/Cheers!

There are only two (2) obvious red flags I would consider:1)  Is the HOA healthy ?  

She said they manage 140 units and that they're not an accounting firm, which leads me to believe her company doesn't have a healthy size staff, she also informed me - that they work extremely hard (even weekends) to disburse funds to owners between the 5th - 10th. 

A healthy economy depends on diversity, and especially support for those large swaths of land used for farming—those little towns like Hollis and Brookline.

I should haveexplaines that the properties have healthy equity positions - 25-35%. 

I want to take that profit to use it to diversify assets and build a healthy rental foundation.I have some short, mid, and long-term goals (as naive as they may be for just starting) as follows:Short-term: Buy 1 property per yearMid-term: $2,500/mo in residual incomeLong-term: Own 1+ multi-tenant propertiesI'm very new to real-estate as an investment outside of the two years I rented my home.