It's come back up but after a couple tenants and a few learning experiences, operations are going well and the capital gains exemption window has expired, so I've left it as a rental even though it's sub-optimal as one (acreage doesn't bring money).Obviously, I've felt the pain and know there's risks.Compromises and optionsI suspect investing activity would require re-deploying of retirement capital as I'm basically barely paying expenses right now on $6k take-home.   

With your SFH did you purchase the property with the garage apartment already converted, or was that something you did yourself after the purchase?

On that note, you might not want to mention to your lender that you intend to move out and convert it to a rental...that would be a major red flag in terms of getting a HELOC.Another big advantage of the HELOC is you only pay if you use the funds, opposed to a cash out refi where you'll be making payments whether you've deployed the capital or not.

We will strip and gut completely, change windows, doors, all systems new, and reconfigure with a  4-5 month completion time on all construction start to finish.

The frames on the windows are wood.

The current owners converted a quadplex to a duplex.

Appears the problem in around the area where the gutter is curved going around the concave turret looking windows interior leak  2nd flloor ceilingoutside view of 2nf/ 3rd floor gutter system some previous treatment some treatmentclose up another viewright now looking for any ideas. 

I brought my property three years back, which I’m planning to convert to a rental property.

On the the other hand, these properties are D class. 2/1 brick duplexes  with gas wall heaters and window units.

I find that hard to believe since nearby comps are selling for $220-$230k for 3/2s fixed up ( my plan was to convert the carport in to a room so it can be a 3 bedroom house).