I budget to replace all large ticket items that will be less than 25% of their remaining life in the next 5 years ie.

At some point, the remodeled kitchen will need to be remodeled again, and the new roof will need to be replaced, and I’ll need new siding, windows, etc.

It does depend on the valuations but there are a couple of options for naming more than 3 potential replacements. 

This study has to be completed every 5 years by an engineering firm licensed to do them.

I currently work Full time as a Computer Network Engineer and looking to invest part time at first.

They wanted $4000 to replace the outside unit. 

When he replaced it there were 9 leaks & is now MIA.

If all major components in the property are new (or recently replaced/upgraded) and you don't have to worry about them for a few years, then not as big of a deal and you can building up the rainy day fund.

Because I believe the cash flow this building will kickoff will feed me for a lifetime.And...30% in capital gains as tax and a $6000 prepayment penalty did not excite me.1031 exchange may of worked, but, it sure is tough to locate a replacement property that would suffice.Thoughts?

If you don't want to deal with lockout simply replace the door knob with a latch that doesn't have a lock (just a doorknob) and keep the deadbolt the only lock with a key on the door.