If your roof was 15 years old, the insurance would be sky-high to factor in the likelihood of damage to the property due to leaks, breakage and disrepair.

Your construction plan will likely be influenced by how many vacancies you have, and if you want to truly use construction financing, it is unlikely that you will be able to complete a project in one year on the south side if you don't have a large amount of vacant units. 

@Varun Maker one factor to consider if you take a HELOC is the impact it can have on your credit score.

If it’s to expensive to switch over how do you factor that into rental prices?

What part of the country are you in as that influences this discussion.

Usually its all about the numbers, however there is other factors that change the play. reach out to me for other insights. id love to chat about it.

Would these factors change the analysis any?

I'm unfamiliar with the process however so not sure if these will apply in this scenario, or if s8 will play a factor.

In y’alls experience, 1) what market factors lead to success in either of these strategies?

There a lot of options out there and many factors to consider.