It started small, just helping to draft LOI's, running down property leads, making calls, but the important thing was just getting in and DOING it. 

If finding a new replacement is more difficult then get your new property under contract first even before your old property closes.  

If you are investing out of state, then do you already have a good property manager lined up? 

TLDR: Quicken (quickbook’s little brother) is super easy, cheap, and still overkill for someone with less than 20 properties.

I do emphasize on showing that my 1800 property is not going to magically become modern. 

It sounds like your current bank might be hesitant to provide a loan for the next property until you can prove that the current property provides enough income to support your overall DTI (Debt to Income Ratio).

I had a flipper come to me asking about doing a new development.He would need $240,000 to purchase the land from a wholesaler and then he would have his GC partner get the construction loan but they cant get the loan if their is someone else that has a lien on the property so i would have to collateralize against one of their assets which they don't have.

:(The system found out that many people were NOT cut out to be property owners.

I have always wrote my own contracts using online templates and I have been asked to write an owner financing contract for someone else.

Through a wholesaler How did you finance this deal?