The house currently rents for $1450/month, we have long-term tenants, and we use a management company.

I would start locallyThere's no substitute for being hands-onand you can't house hack long distance

By securing long-term tenants and maintaining the property’s condition, I’ve enjoyed consistent rental income and significant appreciation in property value.

I believe this is a game of being patient --- long game of 5-10 years to see cashflow especially if you are financing. 

Those present two very different levels of risk.You should also consider how long ago the offense occurred and what the individual has done since then.

I've been flipping for a very long time. 

They also don't factor in how long properties are sitting vacant at that price and also don't factor in how long tenants stay at that price.

Need a new roof in a 3-5 years, you probably want to be pretty liquid (year long CD, Money Market, maybe very short term bond fund etc) for those funds.On a condo board 15 years ago, I  was once able to get us into some nice CD's a decade ago that laddered with the useful life of components.

This process has just begun, and it is unclear how long it may take to get to a resolution.

The plans and specifications for the improvements must be itemized along with an estimate for how long the construction period will last.