I presently own one investment property in Florida. I acquired this property with a VA mortgage which I suppose counts as a conventional mortgage in the context of my question. I'd like to begin adding properties to my portfolio. I'd like to buy my second property by putting 20% down and using a conventional mortgage for the remaining 80% and then following repairs, refinance the property to include the repair costs with a cash-out refinance. My questions are as follows:

-I suppose that refinance loans are considered mortgages.  How many times can I do this before banks won't allow me to refinance future properties?  I've read that Fannie/Freddie sets the limit at 10 but that some banks are more conservative.  Does this apply to refinance loans as well?

-Following the third property (plus the original), how should I go about securing financing?  Should I look for private investors or banks that allow more than four mortgages?

-For those of you with more than four properties, did you flip or wholesale properties to build capital in the beginning?